The Development and Perspective of Dearomatization Reaction

Yuan-Zheng Cheng, Muzi Li, Rui-Xiang Wang, Long-Hao Zhu, Wen-Jie Shen, Xin-Xuan Zou, Qing Gu, Shu-Li You

Prog Chem ›› 2024, Vol. 36 ›› Issue (12) : 1785-1829.

PDF(31989 KB)
Home Journals Progress in Chemistry
Progress in Chemistry

Abbreviation (ISO4): Prog Chem      Editor in chief: Jincai ZHAO

About  /  Aim & scope  /  Editorial board  /  Indexed  /  Contact  / 
PDF(31989 KB)
Prog Chem ›› 2024, Vol. 36 ›› Issue (12) : 1785-1829. DOI: 10.7536/PC241203
Chemistry: A Century of Life-Special Edition

The Development and Perspective of Dearomatization Reaction

Author information +
History +

Abstract

Representing an important class of ubiquitous chemical feedstock, aromatics have been extensively utilized in the nucleophilic aromatic substitution (SNAr) reactions, nitration reactions, Friedel-Crafts alkylation and acylation reactions, cross-coupling reactions, C-H bond functionalization reactions etc. Dearomatization reaction is another type of transformations of aromatics, in which their aromaticity is destroyed or reduced. Since its first report, dearomatization reaction has served as an efficient platform to create C(sp3)-H-rich spiro, fused and bridged polycyclic structures, widely applied in material and medicinal chemistry. In the past two decades, various dearomatization reactions have been established by using transition-metal catalysis, organocatalysis, enzymatic catalysis, photocatalysis, and electrocatalysis. Diverse polycyclic structures have been obtained by the dearomatization of indoles, pyrroles, (benzo)furans, (benzo)thiophenes, quinolines, pyridines, benzenes, naphthalenes, etc. The coupling reagents, including nucleophiles, electrophiles, dipoles, radicals, and carbenes have been developed to assemble different functional groups on dearomative framework. In this review, we briefly summarized the developed dearomatization reactions, which were categorized by the kinds of aromatic compounds. The remaining challenges and perspectives on the future development of dearomatization reactions are also included here.

Contents

1 Introduction

2 Indoles and pyrroles

2.1 Hydrogenation reactions

2.2 Oxidative dearomatization reactions

2.3 Dearomatization reactions with electrophiles

2.4 Dearomatization reactions with nucleophiles

2.5 Dearomatization reactions with radicals

3 Benzofurans and furans

3.1 Dearomatization reactions with nucleophiles

3.2 Dearomatization reactions with electrophiles

3.3 Dearomatization reactions with radicals

3.4 Cycloaddition dearomatization reactions

4 Benzothiophenes and thiophenes

4.1 Hydrogenation reactions

4.2 Dearomatization reactions with nucleophiles

4.3 Dearomatization reactions with electrophiles

4.4 Dearomatization reactions with radicals

4.5 Cycloaddition dearomatization reactions

4.6 Ring expansion dearomatization reactions

4.7 Dearomatization reactions with carbenes

5 Phenols and naphthols

5.1 Hydrogenation reactions

5.2 Oxidative dearomatization reactions

5.3 Dearomatization reactions with nucleophiles

5.4 Dearomatization reactions with electrophiles

5.5 Dearomatization reactions with radicals

5.6 Dearomatization reactions based on η2 or η6 complex

6 Anilines

6.1 Catalytic hydrogenation reactions

6.2 Oxidative dearomatization reactions

6.3 Dearomatization reactions with nucleophiles

6.4 Dearomatization reactions with radicals

6.5 Dearomatization reactions based on η2 complex

7 Pyridines and (iso)quinolines

7.1 Hydrogenation reactions

7.2 Dearomatization reactions with nucleophiles

7.3 Dearomatization reactions with electrophiles

7.4 Dearomatization reactions with dipoles

7.5 Dearomatization reactions with radicals

8 Benzenes and naphthalenes

8.1 Hydrogenation reactions

8.2 Oxidative dearomatization reactions

8.3 Dearomatization reactions with nucleophiles

8.4 Dearomatization reactions with electrophiles

8.5 Dearomatization reactions with radicals

8.6 Cycloaddition dearomatization reactions

8.7 Dearomatization reactions with carbenes

8.8 Rearrangement dearomatization reactions

9 Other arenes

10 Conclusion and outlook

Key words

aromatic compounds / asymmetric catalysis / dearomatization reactions / saturated polycyclic compounds

Cite this article

Download Citations
Yuan-Zheng Cheng , Muzi Li , Rui-Xiang Wang , et al . The Development and Perspective of Dearomatization Reaction[J]. Progress in Chemistry. 2024, 36(12): 1785-1829 https://doi.org/10.7536/PC241203

References

[1]
Auwers K. Ber. Dtsch. Chem. Ges., 1884, 17: 2976.
[2]
Buchner E, Curtius T. Ber. Dtsch. Chem. Ges., 1885, 18: 2377.
[3]
Birch A J. J. Chem. Soc., 1944, 430.
[4]
Blair J M, Bryce-Smith D. Proc. Chem. Soc., 1957, 287.
[5]
Wilzbach K E, Kaplan L. J. Am. Chem. Soc., 1966, 88: 2066.
[6]
Fischer E O. Angew. Chem., 1957, 69: 715.
[7]
Woodward R B, Cava M P, Ollis W D, Hunger A, Daeniker H U, Schenker K. J. Am. Chem. Soc., 1954, 76: 4749.
[8]
Day A C, Nabney J, Scott A I. Proc. Chem. Soc., 1960, 284.
[9]
Ciamician G L, Dennstedt M. Ber. Dtsch. Chem. Ges., 1882, 15: 1831.
[10]
Knorr L, Rabe P, Bufleb H, Jakobi C. Ber. Dtsch. Chem. Ges., 1901, 34: 3491.
[11]
Willsttter R, Hatt D. Ber. Dtsch. Chem. Ges., 1912, 45: 1471.
[12]
Willstätter R, Waldschmidt-Leitz E. Ber. Dtsch. Chem. Ges., 1921, 54: 113.
[13]
Andrews L H, McElvain S M. J. Am. Chem. Soc., 1929, 51: 887.
[14]
Adkins H, Cramer H I. J. Am. Chem. Soc., 1930, 52: 4349.
[15]
Signaigo F K, Adkins H. J. Am. Chem. Soc., 1936, 58: 709.
[16]
Falini G, Gualandi A, Savoia D. Synthesis, 2009, 14: 2440.
[17]
Braun J, Bayer O. Ber. Dtsch. Chem. Ges., 1925. 58: 387.
[18]
Coonradt H, Adkins H. J. Am. Chem. Soc., 1941, 63: 1563.
[19]
Kuwano R, Sato K, Kurokawa T, Karube D, Ito Y. J. Am. Chem. Soc., 2000, 122: 7614.
[20]
Kuwano R, Kashiwabara M, Ohsumi M, Kusano H. J. Am. Chem. Soc., 2008, 130: 808.
[21]
Liu C. Chin. J. Org. Chem., 2024, 44: 1403.
(刘晨光. 有机化学, 2024, 44: 1403.).
[22]
Ketcha D M, Carpenter K P, Zhou Q. J. Org. Chem., 1991, 56: 1318.
[23]
Wang D S, Ye Z S, Chen Q A, Zhou Y G, Yu C B, Fan H J, Duan Y. J. Am. Chem. Soc., 2011, 133: 8866.
[24]
O'Brien S, Smith D C C. J. Chem. Soc., 1960, 4609.
[25]
Remers W A, Gibs G J, Pidacks C, Weiss M J. J. Am. Chem. Soc., 1967, 89: 5513.
[26]
Donohoe T, Guyo P M. J. Org. Chem., 1996, 61: 7664.
[27]
Yang K, Luo Y, Wang C, Qi L W, Fang T, Zhang F, Xu H, Zou L, Li W, Yu P, Song Q. Angew. Chem. Int. Ed., 2020, 59: 3294.
[28]
Beemelmanns C, Blot V, Gross S, Lentz D, Reissig H U. Eur. J. Org. Chem., 2010, 14: 2716.
[29]
Xu P, Würthwein E U, Daniliuc C G, Studer A. Angew. Chem. Int. Ed., 2017, 56: 13872.
[30]
Tsuchiya S, Saito H, Nogi K, Yorimitsu H. Org. Lett., 2019, 21: 3855.
[31]
Finch N, Taylor W I. J. Am. Chem. Soc., 1962, 84: 1318.
[32]
Somei M, Noguchi K, Yamagami R, Kawada Y, Yamada K, Yamada F. Heterocycles, 2000, 53: 7.
[33]
Wearing X Z, Cook J M. Org. Lett., 2002, 4: 4237.
[34]
Jossang A, Jossang P, Hadi H A, Sevenet T, Bodo B. J. Org. Chem., 1991, 56: 6527.
[35]
Wang L, Qu X, Fang L, Li Z, Hu S, Wang F. Eur. J. Org. Chem., 2016, 5494
[36]
Li G, Huang L, Xu J, Sun W, Xie J, Hong L, Wang R. Adv. Synth. Catal., 2016, 358:2873.
[37]
Gao B, Xu S, Du T, Li Y. ChemistrySelect, 2020, 5: 4200.
[38]
Hinman R L, Bauman C P. J. Org. Chem., 1964, 29: 1206.
[39]
Alamgir M, Mitchell P S R, Bowyer P K, Kumar N, Black D S. Tetrahedron, 2008, 64:7136.
[40]
Qian C, Li P, Sun J. Angew. Chem. Int. Ed., 2021, 60: 5871.
[41]
Jiang S Y, Shi J, Wang W, Sun Y, Wu W, Song J R, Yang X, Hao G F, Pan W D, Ren H. ACS Catal., 2023, 13: 3085.
[42]
Chien C, Suzuki T, Kawasaki T, Sakamoto M. Chem. Pharm. Bull., 1984, 32: 3945.
[43]
Buller M J, Cook T G, Kobayashi Y. Heterocycles, 2007, 72: 163.
[44]
Jiang X, Zhu B, Lin K, Wang G, Su W K, Yu C. Org. Biomol. Chem., 2019, 17: 2199.
[45]
Guchhait S K, Chaudary V, Rana V A, Priyadarshani G, Kandekar S, Kashyap M. Org. Lett., 2016, 18: 1534.
[46]
Huang H, Cai J, Ji X, Xiao F, Chen Y, Deng G J. Angew. Chem. Int. Ed., 2016, 55: 307.
[47]
Peng J B, Qi Y, Ma A J, Tu Y Q, Zhang F M, Wang S H, Zhang S Y. Chem. Asian J., 2013, 8: 883.
[48]
Ding X, Dong C L, Guan Z, He Y H. Angew. Chem. Int. Ed., 2019, 58: 118.
[49]
Kolundzic F, Noshi M N, Tjandra M, Movassaghi M, Miller S J. J. Am. Chem. Soc., 2011, 133: 9104.
[50]
An J, Zou Y Q, Yang Q Q, Wang Q, Xiao W J. Adv. Synth. Catal., 2013, 355: 1483.
[51]
Ding W, Zhou Q Q, Xuan J, Li T Y, Lu L Q, Xiao W J. Tetrahedron Lett., 2014, 55: 4648.
[52]
Han L, Zhang W, Shi X X, You S L. Adv. Synth. Catal., 2015, 357: 3064.
[53]
Lin Z, Xue Y, Liang X W, Wang J, Lin S, Tao J, You S L, Liu W. Angew. Chem. Int. Ed., 2021, 60: 8401.
[54]
Zi Y, Cai Z J, Wang S Y, Ji S J. Org. Lett., 2014, 16: 3094.
[55]
Bredenkamp A, Mohr F, Kirsch S F. Synthesis, 2015, 47: 1937.
[56]
Bindu V H, Parvathaneni S P, Rao V J. Catal. Lett., 2017, 147: 1434.
[57]
Wang C P, Jiang G F. Tetrahedron Lett., 2017, 58: 1747.
[58]
Parvathaneni P S, Bikshapathi R, Rao V J. Tetrahedron Lett., 2015, 56: 6385.
[59]
Sriram R, Kumar C N S S P, Raghunandan N, Ramesh V, Sarangapani M, Rao V J. Synth. Commun., 2012, 42: 3419.
[60]
Yadav J S, Reddy B V S, Reddy C S, Krishna A D. Tetrahedron Lett., 2017, 48: 2029.
[61]
Luo J F, Gao S, Ma Y, Ge G. Synlett., 2018, 29: 969.
[62]
Beaucharda A, Laboriea H, Rouillarda H, Lozachb O, Ferandinb Y, Guévelc R L, Guguen-Guillouzoc C, Meijerb L, Bessond T, Thiéry V. Bioorg. Med. Chem., 2009, 17: 6257.
[63]
Pedras M S C, Suchy M, Ahiahonu P W K. Org. Biomol. Chem., 2006, 4: 691.
[64]
Zhang C, Li S, Bures F, Lee R, Ye X, Jiang Z. ACS Catal., 2016, 6: 6853.
[65]
Zhang X, Foote C S. J. Am. Chem. Soc., 1993, 115: 8867.
[66]
Bocchi V, Chierici L, Gardini G P, Mondelli R. Tetrahedron, 1970, 26: 4073
[67]
Alp C, Ekinci D, Gültekin M S, Sentürk M, Sahin E, Küfrevioglu O I. Bioorg. Med. Chem., 2010, 18: 4468.
[68]
Howard J K, Hyland C J T, Just J, Smith J A. Org. Lett., 2013, 15: 1714.
[69]
Lightner D A, Pak C S. J. Org. Chem., 1975, 40: 2724.
[70]
Labroo R B, Labroo V M, King M M, Cohen L A. J. Org. Chem., 1991, 56: 3637.
[71]
Kutney J P, Beck J, Bylsma F, Cook J, Cretney W J, Fuji K, Imhof R, Treasurywala A M. Helv. Chim. Acta., 1975, 58: 1690.
[72]
Darnowski M G, Lanosky T D, Paquette A R, Boddy C N. J. Org. Chem., 2022, 87: 15634.
[73]
Shambalova V E, Larkovich R V, Aldoshin A S, Lyssenko K A, Nechaev M S, Nenajdenko V G. J. Org. Chem., 2024, 89: 11183.
[74]
Hino T, Nakamura T, Nakagawa M. Chem. Pharm. Bull. 1975, 23: 2990.
[75]
Xie W, Jiang G, Liu H, Hu J, Pan X, Zhang H, Wan X, Lai Y, Ma D. Angew. Chem. Int. Ed., 2013, 52: 12924.
[76]
Cabri W, Botta M, Corelli F, Messina F. Tetrahedron Lett., 1975, 38: 3291.
[77]
Zhang Z, Antilla J C. Angew. Chem. Int. Ed., 2012, 51: 11778.
[78]
Atkinson R S, Judkins B D, Russell D R, Sherry L J S. J. Chem. Soc., Perkin Trans. 1, 1985, 1967.
[79]
Jackson A H, Johnson D N, Shannon P V R. J. Chem. Soc., Chem. Commun., 1975, 22: 911.
[80]
Marsden S P, Depew K M, Danishefsky S J. J. Am. Chem. Soc., 1994, 116: 11143.
[81]
Wei Q, Wang Y Y, Du Y L, Gong L Z. Beilstein J. Org. Chem., 2013, 9: 1559.
[82]
Blasdel L K, Lee D E, Sun B, Myers A G. Bioorg. Med. Chem. Lett., 2013, 23: 6905.
[83]
Huang X Y, Xie P P, Zou L M, Zheng C, You S L. J. Am. Chem. Soc., 2023, 145: 11745.
[84]
(a) Fu Y D, Zhang H, Li B B, Huang L, Xiao X, Wang M C, Wei D, Mei G J. Nat. Commun., 2024, 15: 10225.
(b) Miao Y H, Zhang Z X, Huang X Y, Hua Y Z, Jia S K, Xiao X, Wang M C, Xu L P, Mei G J. Chin. Chem. Lett., 2024, 35: 108830.
[85]
Kusama H, Ebisawa M, Funami H, Iwasawa N. J. Am. Chem. Soc., 2009, 131: 16352.
[86]
Romano C, Jia M, Monari M, Manoni E, Bandini M. Angew. Chem. Int. Ed., 2014, 53: 13854.
[87]
Zhang Y Y, Wei Y, Shi M. Org. Lett., 2019, 21: 8250.
[88]
Grugel C P, Breit B. Org. Lett., 2019, 21: 9672.
[89]
Faustino H, Bernal P, Castedo L, López F, Mascareñas J L. Adv. Synth. Catal., 2012, 354: 1658.
[90]
Gao R D, Zhai Y Z, You S L, Ma S M. Org. Chem. Front., 2018, 5: 1664.
[91]
Iwata A, Inuki S, Oishi S, Fujii N, Ohno H. Tetrahedron, 2015, 71: 6580.
[92]
Romano C, Jia M, Monari M, Manoni E, Bandini M. Angew. Chem. Int. Ed., 2014, 53: 13854.
[93]
Kimura M, Futamata M, Mukai R, Tamaru Y. J. Am. Chem. Soc., 2005, 127: 4592.
[94]
Trost B M, Quancard J. J. Am. Chem. Soc., 2006, 128: 6314.
[95]
Wu Q F, He H, Liu W B, You S L. J. Am. Chem. Soc., 2010, 132: 11418.
[96]
Zhao Y, Weix D J. J. Am. Chem. Soc., 2014, 136: 16756.
[97]
Shao W, Li H, Liu C, Liu C J, You S L. Angew. Chem. Int. Ed., 2015, 54: 7684.
[98]
Zhang H J, Gu Q, You S L. Org. Lett., 2019, 21: 9420.
[99]
Zhang X, Yang Z P, Liu C, You S L. Chem. Sci., 2013, 4: 3239.
[100]
Zhuo C X, Zhou Y, You S L. J. Am. Chem. Soc., 2014, 136: 6590.
[101]
Zhuo C X, Liu W B, Wu Q F, You S L. Chem. Sci., 2012, 205.
[102]
Zhuo C X, Cheng Q, Liu W B, Zhao Q, You S L. Angew. Chem. Int. Ed., 2015, 54: 8475.
[103]
Zhu Y, Rawal V H. J. Am. Chem. Soc., 2012, 134: 111.
[104]
Boese R, Sickle A P V, Vollhardt P C. Synthesis, 1994, 12: 1374.
[105]
Liu Y, Xu W, Wang X. Org. Lett., 2010, 12: 1448.
[106]
Cao T, Deitch J, Linton E C, Kozlowski M C. Angew. Chem. Int. Ed., 2012, 51: 2448.
[107]
Zhu Y, He W, Wang W, Pitsch C E, Wang X, Wang X. Angew. Chem. Int. Ed., 2017, 56: 12206.
[108]
Liang G, Ji Y, Liu H, Pang Y, Zhou B, Cheng M, Liu Y, Lin B, Liu Y. Adv. Synth. Catal., 2020, 362: 192.
[109]
Lin X T, Zhao C, Wang D R, Wu G C, Chen G S, Chen S J, Ren H, Deng D S, Xu Y B, Hu X W, Liu Y L. Adv. Synth. Catal., 2022, 364: 890.
[110]
Ikemoto H, Tanaka R, Sakata K, Kanai M, Yoshino T, Matsunaga S. Angew. Chem. Int. Ed., 2017, 56: 7156.
[111]
Staben S T, Kennedy-Smith J J, Toste F D. Angew. Chem. Int. Ed., 2004, 43: 5350.
[112]
Thornton A R, Martin V I, Blakey S B. J. Am. Chem. Soc., 2009, 131: 2434.
[113]
Mizoguchi H, Oikawaa H, Oguri H. Org. Biomol. Chem., 2012, 10: 4236.
[114]
Li L, Chen X M, Wang Z S, Zhou B, Liu X, Lu X, Ye L W. ACS Catal., 2017, 7: 4004.
[115]
Liu J, Zhou L, Zou Y, Wang Q, Goeke A. Org. Biomol. Chem., 2020, 18: 7832.
[116]
Han X Q, Liu J Y, Lu J B, Liang R X, Jia Y X. Org. Lett., 2023, 25: 261.
[117]
Fried F, Taylor J B, Westwood R. J. Chem. Soc. D, 1971, 1226.
[118]
Buechi G, Matsumoto K E, Nishimura H. J. Am. Chem. Soc., 1971, 93: 3299.
[119]
Letcher R M, Choi M C K, Mak T C W, Acheson R M. J. Chem. Soc., Perkin Trans. 1, 1983, 505.
[120]
Jones S B, Simmons B, MacMillan D W C. J. Am. Chem. Soc., 2009, 131: 13606.
[121]
Modha S G, Kumar A, Vachhani D D, Jacobs J, Sharma S K, Parmar V S, Meervelt L V, Van der Eycken E V. Angew. Chem. Int. Ed., 2012, 51: 9572.
[122]
James M J, Cuthbertson J D, O'Brien P, Taylor R J K, Unsworth W P. Angew. Chem. Int. Ed., 2015, 54: 7640.
[123]
Clarke A K, James M J, O'Brien P, Taylor R J K, Unsworth W P. Angew. Chem. Int. Ed., 2016, 55: 13798.
[124]
Zhou Y, Zhuo C X, Gu Q, You S L. Adv. Synth. Catal., 2015, 357: 912.
[125]
Yang J, Wang Z, He Z, Li G, Hong L, Sun W, Wang R. Angew. Chem. Int. Ed., 2020, 59: 642.
[126]
Zhang Y Q, Chen Y B, Liu J R, Wu S Q, Fan X Y, Zhang Z X, Hong X, Ye L W. Nat. Chem., 2021, 13: 1093.
[127]
Birtwistle I, Rogers V. J. Chem. Soc., Perkin Trans. 1, 1987, 1347.
[128]
Davies H M L, Matasi J J, Hodges L M, Huby N J S, Thornley C, Kong N, Houser J H. J. Org. Chem., 1997, 62: 1095.
[129]
Reddy R P, Davies H M L. J. Am. Chem. Soc., 2007, 129: 10312.
[130]
Mulcahy J V, Bois J D. J. Am. Chem. Soc., 2008, 130: 12630.
[131]
Lian Y, Davies H M L. J. Am. Chem. Soc., 2010, 132: 440.
[132]
Ueda J, Harada S, Kanda A, Nakayama H, Nemoto T. J. Org. Chem., 2020, 85: 10934.
[133]
Barton D H R, Finet J P, Giannotti C, Halley F. J. Chem. Soc., Perkin Trans. 1, 1987, 241.
[134]
Chahma M, Combellas C, Thiebault A. J. Org. Chem., 1995, 60: 8015.
[135]
Mingoia F. Tetrahedron, 2001, 57: 10147.
[136]
Bedford R B, Fey N, Haddowa M F, Sankey R F. Chem. Commun., 2011, 47: 3649.
[137]
Wu K J, Dai L X, You S L. Org. Lett., 2012, 14: 3772.
[138]
Shen C, Liu R R, Fan R J, Li Y L, Xu T F, Gao J R, Jia Y X. J. Am. Chem. Soc., 2015, 137: 4936.
[139]
Marchese A D, Lind F, Mahon Á E, Yoon H, Lautens M. Angew. Chem. Int. Ed., 2019, 58: 5095.
[140]
Chu H, Cheng J, Yang J, Guo Y L, Zhang J. Angew. Chem. Int. Ed., 2020, 59: 21991.
[141]
Nie Y H, Komatsuda M, Yang P, Zheng C, Yamaguchi J, You S L. Org. Lett., 2022, 24: 1481.
[142]
Polák P, Tobrman T. Org. Lett., 2017, 19: 4608.
[143]
Yamaguchi M, Fujiwara S, Manabe K. Org. Lett., 2019, 21: 6972.
[144]
Izmer V V, Lebedev A Y, Kononovich D S, Borisov I S, Kulyabin P S, Goryunov G P, Uborsky D V, Canich J A M, Voskoboynikov A Z. Organometallics, 2019, 38: 4645.
[145]
Yamaguchi M, Fujiwara S, Mori Y, Konishi H, Manabe K. Tetrahedron, 2022, 123: 132962.
[146]
Wu K J, Dai L X, You S L. Chem. Commun., 2013, 49: 8620.
[147]
Szmuszkovicz J. J. Org. Chem., 1962, 27: 511.
[148]
Wang L, Shao Y, Liu Y. Org. Lett., 2012, 14: 3978.
[149]
Vedejs E, Little J D. J. Org. Chem., 2003, 69: 1794.
[150]
Hill J E, Lefebvre Q, Fraser L A, Clayden J. Org. Lett., 2018, 20: 5770.
[151]
Chataigner I, Hess E, Toupet L, Piettre S R. Org. Lett., 2001, 3: 515.
[152]
Chataigner I, Piettre S R. Org. Lett., 2007, 9: 4159.
[153]
Kishbaugh T L S, Gribble G W. Tetrahedron Lett., 2001, 42: 4738.
[154]
Andreini M, Paolis M D, Chataigner I. Catal. Commun., 2015, 63: 15.
[155]
Andreini M, Chapellas F, Diab S, Pasturaud K, Piettre S R, Legros J, Chataigner I. Org. Biomol. Chem., 2016, 14: 2833.
[156]
Biolatto B, Kneeteman M, Paredes E, Mancini P E. J. Org. Chem., 2001, 66: 3906.
[157]
Carmen de la Fuente M, Domínguez D. Tetrahedron, 2011, 67: 3997.
[158]
Kubota K, Hayama K, Iwamoto H, Ito H. Angew. Chem. Int. Ed., 2015, 54: 8809.
[159]
Hayama K, Kubota K, Iwamoto H, Ito H. Chem. Lett., 2017, 46: 1800.
[160]
Chen L, Shen J J, Gao Q, Xu S. Chem. Sci., 2018, 9: 5855.
[161]
Shi Y, Gao Q, Xu S. J. Org. Chem., 2018, 83: 14758.
[162]
Hayama K, Kojima R, Kubota K, Ito H. Org. Lett., 2020, 22: 739.
[163]
Hayama K, Takahashi R, Kubota K, Ito H. Chem. Lett., 2021, 50: 289.
[164]
Trammel G L, Kuniyil R, Crook P F, Liu P, Brown M K. J. Am. Chem. Soc., 2021, 143: 16502.
[165]
Pelkey E T, Gribble G W. Synthesis, 1999, 1117.
[166]
Awata A, Arai T. Angew. Chem. Int. Ed., 2014, 53: 10462.
[167]
Gerten A L, Stanley L M. Org. Chem. Front., 2016, 3: 339.
[168]
Lee S, Diab S, Queval P, Sebban M, Chataigner I, Pittre S R. Chem. Eur. J., 2013, 19: 7181.
[169]
Liu X, Yang D, Wang K, Zhang J, Wang R. Green Chem., 2017, 19: 82.
[170]
Osipov D, Demidov M R, Artemenko A A, Rashchepkina D A, Krasnikov P E, Osyanin V A. J. Org. Chem., 2024, 89: 9816.
[171]
Trost B M, Ehmke V, O’Keefe B M, Bringley D A. J. Am. Chem. Soc., 2014, 136: 8213.
[172]
Laugeois M, Ling J, Férard C, Michelet V, Ratovelomanana-Vidal V, Vitale M R. Org. Lett., 2017, 19: 2266.
[173]
Sun M, Zhu Z Q, Gu L, Wan X, Mei G J, Shi F. J. Org. Chem., 2018, 83: 2341.
[174]
Rivinoja D J, Gee Y S, Gardiner M G, Ryan J H, Hyland C T. ACS Catal., 2017, 7: 1053.
[175]
Suo J J, Liu W, Du J, Ding C H, Hou X L. Chem. Asian J., 2018, 13: 959.
[176]
Zhang J Q, Tong F, Sun B B, Fan W T, Chen J B, Hu D, Wang X W. J. Org. Chem., 2018, 83: 2882.
[177]
Chen Q, Zhang F, Cai Y, Guo Y L, You S L. Angew. Chem. Int. Ed., 2018, 57: 2134.
[178]
Dou P H, Yuan S P, Chen Y, Zhao J Q, Wang Z H, You Y, Zhang Y P, Zhou M Q, Yuan W C. J. Org. Chem., 2022, 87: 6025.
[179]
Cerveri A, Nieto Faza O, Silva López C, Grilli S, Bandini M. J. Org. Chem., 2019, 84: 6347.
[180]
Birbaum L, Gillard L, Gerard H, Oulyadi H, Vincent G, Moreau X, De Paolis M, Chataigner I. Chem. Eur. J., 2019, 25: 13688.
[181]
Jin L W, Jiang F, Chen K W, Du B X, Mei G J, Shi F. Org. Biomol. Chem., 2019, 17: 3894.
[182]
Liu K, Wang G, Cheng S J, Jiang W F, He C, Ye Z S. Tetrahedron Lett., 2019, 60: 1885.
[183]
Li K, Gonçalves T P, Huang K W, Lu Y. Angew. Chem. Int. Ed., 2019, 58: 5427.
[184]
Wang H, Zhang J, Tu Y, Zhang J. Angew. Chem. Int. Ed., 2019, 58: 5422.
[185]
Zhao J Q, Wu Z J, Zhou M Q, Xu Y Y, Zhang X M, Yuan W C. Org. Lett., 2015, 17: 5020.
[186]
Mei M S, Wang Y H, Hu Q, Li Q H, Shi D Y, Gao D, Ge G, Lin G Q, Tian P. Chem. Commun., 2020, 56: 10718.
[187]
Huang H, Li Q Z, Liu Y Q, Leng H J, Xiang P, Dai Q S, He X H, Huang W, Li J L. Org. Chem. Front., 2020, 7: 3862.
[188]
Yue D F, Zhao J Q, Chen X Z, Zhou Y, Zhang X M, Xu X Y, Yuan W C. Org. Lett., 2017, 19: 5020.
[189]
Zou W L, Liu Y Q, Li Q Z, Kou X X, Huang H, Tong R S, Li J L, Han B. Org. Chem. Front., 2023, 7: 1237.
[190]
Wan Q, Xie J H, Zheng C, Yuan Y F, You S L. Angew. Chem. Int. Ed., 2021, 60: 19730.
[191]
Yuan W C, Chen X M, Zhao J Q, Zhang Y P, Wang Z H, You Y. Org. Lett., 2022, 24: 826.
[192]
Xie J H, Zheng C, You S L. Angew. Chem. Int. Ed., 2021, 60: 22184.
[193]
Kwon S, Kuroki N. Chem. Lett., 1980, 9: 237.
[194]
Takayama H, Misawa K, Okada N, Ishikawa H, Kitajima M, Hatori Y, Murayama T, Wongseripipatana S, Tashima K, Matsumoto K, Horie S. Org. Lett., 2006, 8: 5705.
[195]
Silva L F Jr, Craveiro M V, Gambardella M T P. Synthesis, 2007, 3851.
[196]
Liu Q, Zhao Q Y, Liu J, Wu P, Yi H, Lei A. Chem. Commun., 2012, 48: 3239
[197]
Hodson H F, Smith G F. J. Chem. Soc., 1957, 3544.
[198]
Tajima N, Hayashi T, Nakatsuka S N. Tetrahedron Lett. 2000, 41: 1059.
[199]
Beaud R, Guillot R, Kouklovsky C, Vincent G. Angew. Chem. Int. Ed., 2012, 51: 12546.
[200]
Sabat N, Zhou W, Gandon V, Guinchard X, Vincent G. Angew. Chem. Int. Ed., 2022, 61: e202204400.
[201]
Julian D, Foster R. J. Chem. Soc. Chem. Commun., 1973, 311.
[202]
Ikeda M, Ohno K, Mohri S i, Takahashi M, Tamura Y. J. Chem. Soc. Perkin Trans. I, 1984, 405.
[203]
Andrew D, Hastings D J, Oldroyd D L, Rudolph A, Weedon A C, Wong D F, Zhang B. Pure Appl. Chem., 1992, 64: 1327.
[204]
Zhu M, Zheng C, Zhang X, You S L. J. Am. Chem. Soc., 2019, 141: 2636.
[205]
Oderinde M S, Mao E, Ramirez A, Pawluczyk J, Jorge C, Cornelius L A M, Kempson J, Vetrichelvan M, Pitchai M, Gupta A, Gupta A K, Meanwell N A, Mathur A, Dhar T G M. J. Am. Chem. Soc., 2020, 142: 3094.
[206]
Zhang Z, Yi D, Zhang M, Wei J, Lu J, Yang L, Wang J, Hao N, Pan X, Zhang S, Wei S, Fu Q. ACS Catal., 2020, 10: 10149.
[207]
Li H, He Y, Zhang D, Yang L, Zhang J, Long R, Lu J, Wei J, Yang L, Wei S, Yi D, Zhang Z, Fu Q. Chem. Commun., 2022, 58: 3194.
[208]
Rolka A B, Koenig B. Org. Lett. 2020, 22: 5035.
[209]
Arai N, Ohkuma T. J. Org. Chem., 2020, 85: 15717.
[210]
Popescu M V, Mekereeya A, Alegre-Requena J V, Paton R S, Smith M D. Angew. Chem. Int. Ed., 2020, 59: 23020.
[211]
Strieth-Kalthoff F, Henkel C, Teders M, Kahnt A, Knolle W, Gómez-Suárez A, Dirian K, Alex W, Bergander K, Daniliuc C G, Abel B, Guldi D M, Glorius F. Chem, 2019, 5: 2183.
[212]
Ma J, Schäfers F, Daniliuc C, Bergander K, Strassert C A, Glorius F. Angew. Chem. Int. Ed., 2020, 59: 9639.
[213]
Oderinde M S, Ramirez A, Dhar T G M, Cornelius L A M, Jorge C, Aulakh D, Sandhu B, Pawluczyk J, Sarjeant A A, Meanwell N A, Mathur A, Kempson J. J. Org. Chem., 2021, 86: 1730.
[214]
Hou L, Yang L, Yang G, Luo Z, Xiao W, Yang L, Wang F, Gong L Z, Liu X, Cao W, Feng X. J. Am. Chem. Soc., 2024, 146: 23457.
[215]
Wang J, Fu Q, Cao S, Lv X, Yin Y, Ban X, Zhao X, Jiang Z. J. Am. Chem. Soc., 2024, 146: 22840.
[216]
Zhu M, Huang X L, Xu H, Zhang X, Zheng C, You S L. CCS Chem., 2020, 2: 652.
[217]
Zhu M, Zhang X, Zheng C, You S L. ACS Catal., 2020, 10: 12618.
[218]
Mateos J, Vega-Peñaloza A, Franceschi P, Rigodanza F, Andreetta P, Companyó X, Pelosi G, Bonchio M, Dell’Amico L. Chem. Sci., 2020, 11: 6532.
[219]
Zhu M, Xu H, Zhang X, Zheng C, You S L. Angew. Chem. Int. Ed., 2021, 60: 7036.
[220]
Zhu M, Huang X L, Sun S, Zheng C, You S L. J. Am. Chem. Soc., 2021, 143: 13441.
[221]
Arai N, Ohkuma T. Tetrahedron Lett., 2022, 88: 153588.
[222]
Mühmel S, Alpers D, Hoffmann F, Brasholz M. Chem. Eur. J., 2015, 21: 12308.
[223]
Alpers D, Gallhof M, Witt J, Hoffmann F, Brasholz M. Angew. Chem. Int. Ed., 2017, 56: 1402.
[224]
Wang Q, Qu Y, Xia Q, Song H, Song H, Liu Y, Wang Q. Adv. Synth. Catal., 2018, 360: 2879.
[225]
Zhou W J, Wang Z H, Liao L L, Jiang Y X, Cao K G, Ju T, Li Y, Cao G M, Yu D G. Nat. Commun., 2020, 11: 3263.
[226]
Gao X, Yuan Y, Xie X, Zhang Z. Chem. Commun., 2020, 56: 14047.
[227]
Ho H E, Pagano A, Rossi-Ashton J A, Donald J R, Epton R G, Churchill J C, James M J, O’Brien P, Taylor R J K, Unsworth W P. Chem. Sci., 2020, 11: 1353.
[228]
Zhang Y, Ji P, Gao F, Huang H, Zeng F, Wang W. ACS Catal., 2021, 11: 998.
[229]
Inprung N, Ho H E, Rossi-Ashton J A, Epton R G, Whitwood A C, Lynam J M, Taylor R J K, James M J, Unsworth W P. Org. Lett., 2022, 24: 668.
[230]
Mei L, Moutet J, Stull S M, Gianetti T L. J. Org. Chem., 2021, 86: 10640.
[231]
Mo K D, Zhou X C, Wu J, Zhao Y F. Org. Lett., 2022, 24: 2788.
[232]
Lan J Y, Li S Y, Lin K J, Zhou P, Chen W L, Gao L Q, Zhu T S. Org. Biomol. Chem., 2022, 20: 3475.
[233]
Mo K, Zhou X, Wu J, Zhao Y. J. Org. Chem., 2022, 87: 16106.
[234]
Mo K D, Zhou X C, Wang J, Wu J, Zhao Y F. Org. Lett., 2023, 25: 3956.
[235]
Royer J, Planas L, Martens T, Billon-Souquet F. Heterocycles, 2004, 63: 765.
[236]
Wu J, Dou Y, Guillot R, Kouklovsky C, Vincent G. J. Am. Chem. Soc., 2019, 141: 2832.
[237]
Liu X, Yang D, Liu Z, Wang Y, Liu Y, Wang S, Wang P, Cong H, Chen Y H, Lu L, Qi X, Yi H, Lei A. J. Am. Chem. Soc., 2023, 145: 3175.
[238]
Zhao W, Lu Y, Qiao Y, Yin X, Liu C, Fang Z, Zhu J, Guo K. Org. Lett., 2023, 25: 7451.
[239]
Gentry E C, Rono L J, Hale M E, Matsuura R, Knowles R R. J. Am. Chem. Soc., 2018, 140: 3394.
[240]
Liang K, Tong X, Li T, Shi B, Wang H, Yan P, Xia C. J. Org. Chem., 2018, 83: 10948.
[241]
Cheng Y Z, Zhao Q R, Zhang X, You S L. Angew. Chem. Int. Ed., 2019, 58: 18069.
[242]
Shi J, Li X J, Jiang S Y, Wu W, Ren H. ACS Catal., 2024, 14: 5605.
[243]
Deng Z, Meng L, Bing X, Niu S, Zhang X, Peng J, Luan Y X, Chen L, Tang P. J. Am. Chem. Soc., 2024, 146: 2325.
[244]
Zhang W Y, Wang H C, Wang Y, Zheng C, You S L. J. Am. Chem. Soc., 2023, 145: 10314.
[245]
Piancatel G, Scettri A, Barbadoro S. Tetrahedron Lett., 1976, 39: 3555.
[246]
Yin B, Lai J, Zhang Z, Jiang H. Adv. Synth. Catal., 2011, 353: 1961.
[247]
Liu J, Peng H, Lu L, Xu X, Jiang H, Yin B. Org. Lett., 2016, 18: 6440.
[248]
Li J, Peng H, Wang F, Wang X, Jiang H, Yin B. Org. Lett., 2016, 18: 3226.
[249]
Sperry J B, Ghiviriga I, Wright D L. Chem. Commun., 2006, 194.
[250]
Yang Y, Fei C, Wang K, Liu B, Jiang D, Yin B. Org. Lett., 2018, 20: 2273.
[251]
Yang Y, Huang L, Jiang K, Cao X, Yin B. Org. Lett., 2022, 24: 3275.
[252]
Yu X, Meng Q Y, Daniliuc C G, Studer A. J. Am. Chem. Soc., 2022, 144: 7072.
[253]
Luo W, Jiang K, Yin B. Chin. J. Chem., 2022, 40: 2893.
[254]
Mukhina O A, Kuznetsov D M, Cowger T M, Kutateladze A G. Angew. Chem. Int. Ed., 2015, 54: 11516.
[255]
Lei L, Yao Y Y, Jiang L J, Lu X, Liang C, Mo D L. J. Org. Chem., 2020, 85: 3059.
[256]
Hu N, Jung H, Zheng Y, Lee J, Zhang L, Ullah Z, Xie X, Harms K, Baik M, Meggers E. Angew. Chem. Int. Ed., 2018, 57: 6242.
[257]
Liao Z Y, Gao F, Ye Y H, Yu Q H, Yang C, Luo Q Y, Du F, Pan B, Zhong W W, Liang W. Chem. Commun., 2024, 60: 4455.
[258]
Cheng Q, Zhang H J, Yue W J, You S L. Chem, 2017, 3: 428.
[259]
Xu X, Zhong Y, Xing Q, Gao Z, Gou J, Yu B. Org. Lett., 2020, 22: 5176.
[260]
Cheng G, Zhao P, Su H, Wahab A, Gao Z, Gou J, Yu B. J. Org. Chem., 2024, 89: 4349
[261]
Dai X, Zhang F, Dai L, Lu Y. CCS Chem., 2023, 5: 2023.
[262]
Borowski A F, Sabo-Etienne S, Donnadieu B, Chaudret B. Organometallics, 2003, 22: 4803.
[263]
Urban S, Beiring B, Ortega N, Paul D, Glorius F. J. Am. Chem. Soc., 2012, 134: 15241.
[264]
Tan G, You Q, Lan J, You J. Angew. Chem. Int. Ed., 2018, 57: 6309.
[265]
Li X, Duan M, Yu P, Houk K N, Sun J. Nat. Commun., 2021, 12: 4881.
[266]
Shi Z, Wang W Z, Li N, Yuan Y, Ye K. Org. Lett., 2022, 24: 6321.
[267]
Ji P, Meng X, Chen J, Gao F, Xu H, Wang W. Chem. Sci., 2023, 14: 3332.
[268]
Yu H, Sercel Z P, Rezgui S P, Farhi J, Virgil S C, Stoltz B M. J. Am. Chem. Soc., 2023, 145: 25533.
[269]
Tohti A, Lerda V, Stokes B J. Synlett, 2024, 35: 1311.
[270]
Zhao Z, Li Y, Jia S, Peng L, Zhang Z, Wu F, Wang P, Qin W, Lan Y, Yan H. Chem. Sci., 2024, 15: 14295.
[271]
Zheng Y, Chen Y, He Y, Rizzo A, Zhou Y, Low K H, Krenske E H, Chiu P. Angew. Chem. Int. Ed., 2024, 63: e202407059.
[272]
Lei N, Zhang Q, Tao P, Lu C, Lei Q, Zheng K. Org. Chem. Front., 2024, 11: 4654.
[273]
(a) Reinecke M G, Mazza D D. J. Org. Chem., 1989, 54: 2142.
(b) Callander D D, Coe P L, Tatlow J C. J. Chem. Soc. Chem. Commun., 1966, 143.
(c) Zhang M X, Shan W, Chen Z, Yin J, Yu G A, Liu S H. Tetrahedron Lett., 2015, 56: 6833.
[274]
Okitsu T, Shinohara Y, Luo H, Hatano M, Yakura T. Chem Asian J., 2024, 19: e202301031.
[275]
Tagmazyan K Ts, Mkrtchyan R S, Babayan A T. Arm. Khim. Zh., 1974, 37: 587.
[276]
Zhen G, Zeng G, Jiang K, Wang F, Cao X, Yin B. Chem. Eur. J., 2023, 29, e202203217.
[277]
Zhen G, Zeng G, Wang F, Cao X, Yin B. Adv. Synth. Catal., 2023, 365: 43.
[278]
Chiminelli M, Scarica G, Serafino A, Marchiò L, Viscardi R, Maestri G. Molecules, 2024, 29: 595.
[279]
Sanches-Delgado R A. Organo metallic Modeling of the Hydrodesulphurization and Hydrodenitrogenation Reactions; Kluwer Academic Publishers: Dordrecht, 2002.
[280]
Jones W D, Dong L. J. Am. Chem. Soc., 1991, 113: 559.
[281]
For review, see: Wang L, He W, Yu Z. Chem. Soc. Rev., 2013, 42: 599.
[282]
Inami T, Takahashi T, Kurahashi T, Matsubara S. J. Am. Chem. Soc., 2019, 141: 12541.
[283]
Wang H, Shao H, Das A, Dutta S, Chan H T, Daniliuc C, Houk K N, Glorius F. Science, 2023, 381: 75.
[284]
Yanagimoto A, Uwabe Y, Wu Q, Muto M, Yamaguchi J. ACS Catal., 2021, 11: 10429.
[285]
Corey E J, Girotra N N, Mathew C T. J. Am. Chem. Soc., 1969, 91: 1557.
[286]
Stork G, Foreman L. J. Am. Chem. Soc., 1946, 68: 2172.
[287]
Zhang Y, Liao Y T, Liu X H, Xu X, Lin L L, Feng X M. Chem. Sci., 2017, 8: 6645.
[288]
Kulish K, Boldrini C, Castineira R M, Perez J M, Harutyunyan S R. Chem. Eur. J., 2020, 26: 15843.
[289]
Kürti L, Herczegh P, Visy J, Simonyi M, Antus S, Pelter A. J. Chem. Soc., Perkin Trans. 1, 1999, 379.
[290]
Liu Q, Rovis T. J. Am. Chem. Soc., 2006, 128: 2552
[291]
Boppisetti J K, Birman V B. Org. Lett., 2009, 11: 1221.
[292]
Volp K A, Harned A M. Chem. Commun., 2013, 49: 3001.
[293]
Guérard K C, Sabot C, Beaulieu M A, Giroux M A, Canesi S. Tetrahedron, 2010, 66: 5893.
[294]
Portalier F, Bourdreux F, Marrot J, Moreau X, Coeffard V, Greck C. Org. Lett., 2013, 15: 5642.
[295]
Dohi T, Maruyama T A, Takenaga N, Senami K, Minamitsuji Y, Fujioka H, Caemmerer S B, Kita Y. Angew. Chem. Int. Ed., 2008, 47: 3787.
[296]
Uyanik M, Yasui T, Ishihara K. Angew. Chem. Int. Ed., 2010, 49: 2175.
[297]
Zheng H L, Cai L, Pan M, Uyanik M, Ishihara K, Xue X S. J. Am. Chem. Soc., 2023, 145: 7301.
[298]
Dohi T, Takenaga N, Nakae T, Toyoda Y, Yamasaki M, Shiro M, Fujioka H, Maruyama A, Kita Y. J. Am. Chem. Soc., 2013, 135: 4558.
[299]
Zheng H L, Sang Y Q, Houk K N, Xue X S, Cheng J P. J. Am. Chem. Soc., 2019, 141: 16046.
[300]
Zhu J, Grigoriadis N P, Lee J P, Porco J A. J. Am. Chem. Soc., 2005, 127: 9342.
[301]
Rudolph A, Bos P H, Meetsma A, Minnaard A J, Feringa B L. Angew. Chem. Int. Ed., 2011, 50: 5834.
[302]
Oguma T, Katsuki T. J. Am. Chem. Soc., 2012, 134: 20017.
[303]
Zhu G M, Bao G J, Li Y P, Yang J X, Sun W S, Li j, Hong L, Wang R. Org. Lett., 2016, 18: 5288.
[304]
Mei G J, Luo Y, Koay W L, Li R, Lan Y, Lu Y. Chem. Catal., 2022, 2: 386.
[305]
Gao X, Han T J, Li B B, Hou X X, Hua Y Z, Jia S K, Xiao X, Wang M C, Wei D, Mei G J. Nat. Commun., 2023, 14: 5189.
[306]
Jia M Q, You S L. Chem. Commun., 2012, 48: 6363.
[307]
Seoane A, Casanova N, Quiñones N, Mascareñas J L, Gulías M. J. Am. Chem. Soc., 2014, 136: 7607.
[308]
Nemoto T, Matsuo N, Hamada Y. Adv. Synth. Catal., 2014, 356: 2417.
[309]
Ding L, Wu W T, Zhang L M, You S L. Org. Lett., 2020, 22: 5861.
[310]
Zhao K, Kohnke P, Yang Z G, Cheng X P, You S L, Zhang L M. Angew. Chem. Int. Ed., 2022, 61, e202207518.
[311]
Yang D X, Wnag L Q, Kai M, Li D, Yao X J, Wang R. Angew. Chem. Int. Ed., 2015, 54: 9523.
[312]
Yang D X, Wang L Q, Han F X, Li D, Zhuo D P, Wang R. Angew. Chem. Int. Ed., 2015, 54: 2185.
[313]
Wang S G, Liu X J, Zhao Q C, Zheng C, Wang S B, You S L. Angew. Chem. Int. Ed., 2015, 54: 14929.
[314]
Liu X H, Wang P X, Bai L T, Li D, Wang L Q, Yang D X, Wang R. ACS Catal., 2018, 8: 10888.
[315]
Wang L Q, Yang D X, Li D, Zhu H Y, Wang P X, Liu X H, Bai L T, Wang R. Adv. Synth. Catal., 2018, 360: 4491.
[316]
Baker R J, Ching J, Hou T R, Franzoni I, Lautens M. Angew. Chem., 2022, 134: e202116171.
[317]
Nemoto T, Ishige Y, Yoshida M, Kohno Y, Kanematsu M, Hamada Y. Org. Lett., 2010, 12: 5020.
[318]
Rousseaux S, García-Fortanet J, Del Aguila Sanchez M A, Buchwald S L. J. Am. Chem. Soc., 2011, 133: 9282.
[319]
Xu R Q, Gu Q, Wu W T, Zhao Z A, You S L. J. Am. Chem. Soc., 2014, 136: 15469.
[320]
Wu Q F, Liu W B, Zhuo C X, Rong Z Q, Ye K Y, You S L. Angew. Chem. Int. Ed., 2011, 50: 4455.
[321]
Schmidt B, Berger R, Kelling A, Schilde U. Chem. Eur. J., 2011, 17: 7032.
[322]
Zhuo C X, You S L. Angew. Chem. Int. Ed., 2013, 52: 10056.
[323]
Zhuo C X, You S L. Adv. Synth. Catal., 2014, 356: 2020.
[324]
Tu H F, Zheng C, Xu R Q, Liu X J, You S L. Angew. Chem. Int. Ed., 2017, 56: 3237.
[325]
Shen D, Chen Q L, Yan P P, Zeng X F, Zhong G F. Angew. Chem. Int. Ed., 2017, 56: 3242.
[326]
Cheng Q, Wang Y, You S L. Angew. Chem. Int. Ed., 2016, 55: 3496.
[327]
Xu R Q, Yang P, Tu H F, Wang S G, You S L. Angew. Chem. Int. Ed., 2016, 55: 15137.
[328]
Xu R Q, Gu Q, You S L. Angew. Chem. Int. Ed., 2017, 56: 7252.
[329]
Liang W B, Yang Y D, Yang M F, Zhang M, Li C M, Ran Y, Lan J B, Bin Z Y, You J S. Angew. Chem. Int. Ed., 2021, 60: 3493.
[330]
Kadarauch M, Whalley D M, Phipps R J. J. Am. Chem. Soc., 2023, 145: 25553.
[331]
Shao L, Hu X P. Chem. Commun., 2017, 53: 8192.
[332]
Du K, Guo P, Chen Y, Cao Z, Wang Z, Tang W. Angew. Chem. Int. Ed., 2015, 54: 3033.
[333]
Yang L, Zheng H, Luo L, Nan J, Liu J, Wang Y, Luan X J. J. Am. Chem. Soc., 2015, 137: 4876.
[334]
Luo L, Zheng H, Liu J, Wang H, Wang Y, Luan X J. Org. Lett., 2016, 18: 2082.
[335]
Nan J, Zuo Z J, Luo L, Bai L, Zheng H Y, Yuan Y N, Liu J J, Luan X J. J. Am. Chem. Soc., 2013, 135: 17306.
[336]
Zheng J, Wang S B, Zheng C, You S L. J. Am. Chem. Soc., 2015, 137: 4880.
[337]
Yang L, Zheng H Y, Luo L, Nan J, Liu J J, Wang Y Y, Luan X J. J. Am. Chem. Soc., 2015, 137: 4876.
[338]
Zuo Z J, Wang H, Fan L X, Liu J J, Wang Y Y, Luan X J. Angew. Chem. Int. Ed., 2017, 56: 2767.
[339]
Tan B J, Bai L, Ding P, Liu J J, Wang Y Y, Luan X J. Angew. Chem. Int. Ed., 2019, 58: 1474.
[340]
Zuo Z J, Wang J, Liu J J, Wang Y Y, Luan X J. Angew. Chem. Int. Ed., 2020, 59: 653.
[341]
Phipps R J, Toste F D. J. Am. Chem. Soc., 2013, 135: 1268.
[342]
Yin Q, Wang S G, Liang X W, Gao D W, Zheng J, You S L. Chem. Sci., 2015, 6: 4179.
[343]
Wang Y F, Shao J J, Wang B, Chu M M, Qi S S, Du X H, Xu D Q. Adv. Synth. Catal., 2018, 360: 2285.
[344]
Wang P X, Wang J, Wang L Q, Li D, Wang K Z, Liu Y Y, Zhu H Y, Liu X H, Yang D X, Wang R. Adv. Synth. Catal., 2018, 360: 401.
[345]
Guo Q P, Wang M R, Liu H, Wang R, Xu Z Q. Angew. Chem. Int. Ed., 2018, 57: 4747.
[346]
Wang S G, Yin Q, Zhuo C X, You S L. Angew. Chem. Int. Ed., 2015, 54: 647.
[347]
Nan J, Liu J J, Zheng H Y, Zuo Z J, Hou L, Hu H M, Wang Y Y, Luan X J. Angew. Chem. Int. Ed., 2015, 54: 2356.
[348]
Wu D Q, Guan Z Y, Peng Y, Sun J, Zhong C, Deng H. Adv. Synth. Catal., 2018, 360: 4720.
[349]
(a) Xia Z L, Zheng C, Xu R Q, You S L. Nat. Commun., 2019, 10: 3150.
(b) Chen Y, Jia S K, Xiao X, Wang M C, Huang L, Mei G J. Org. Lett., 2023, 25: 4740.
(c) Li Y Y, Yang F Y, Wu M Y, Huang L, Mei G J. Adv. Synth. Catal., 2024, 366: 4238.
[350]
Nakayama H, Harada S, Kono M, Nemoto T. J. Am. Chem. Soc., 2017, 139: 10188.
[351]
(a) Guo Y L, Wang D H. ACS Catal., 2019, 9: 7343.
(b) Yihuo A, Pu M, Tan Z, Liao J, Tan J, Zhou Q L, Liu X, Feng X. Sci. China Chem., 2024, 67: 2694.
[352]
Kakiuchi K, Yamaguchi B, Kinugawa M, Ue M, Tobe Y, Odaira Y. J. Org. Chem., 1993, 58: 2797.
[353]
Han G, Liu Y, Wang Q. Org. Lett., 2014, 16: 3188.
[354]
Hu B, Li Y, Dong W, Ren K, Xie X, Wan J, Zhang Z. Chem. Commun., 2016, 52: 3709.
[355]
James M J, Schwarz J L, Strieth-Kalthoff F, Wibbeling B, Glorius F. J. Am. Chem. Soc., 2018, 140: 8624.
[356]
Dutta S, Lee D, Ozols K, Daniliuc C G, Shintani R, Glorius F. J. Am. Chem. Soc., 2024, 146: 2789.
[357]
Zhang Z, Tang X, Thomoson C S, Dolbier W R. Org. Lett., 2015, 17: 3528.
[358]
Hu B, Li Y, Dong W, Ren K, Xie X, Wan J, Zhang Z. Chem. Commun., 2016, 52: 3709.
[359]
Dong W, Yuan Y, Gao X, Keranmu M, Li W, Xie X, Zhang Z. Org. Lett., 2018, 20: 5762.
[360]
Habert L, Cariou K. Angew. Chem. Int. Ed., 2021, 60: 171.
[361]
Zhang C, Bu F, Zeng C, Wang D, Lu L, Zhang H, Lei A. CCS Chem., 2021, 4: 1199.
[362]
Winemiller M D, Kopach M E, Harman W D. J. Am. Chem. Soc., 1997, 119: 2096.
[363]
Keane J M, Chordia M D, Mocella C J, Sabat M, Trindle C O, Harman W D. J. Am. Chem. Soc., 2004, 126: 6806.
[364]
Kündig E P, Sau M, Perez-Luna A. Synlett, 2006, 2006: 2114.
[365]
Weatherford-Pratt J T, Bloch J M, Smith J A, Eric son M N, Siela D J, Ortiz M R, Shingler M H, Fong S, Laredo J A, Patel I U, McGraw M, Dickie D A, Harman W D. Sci. Adv., 2014, 10, eadl0885.
[366]
Rasero-Almansa A M, Corma A, Iglesias M, Sánchez F. Green Chem., 2014, 16: 3522.
[367]
Shriner R L, Struck H C, Jorison W J. J. Am. Chem. Soc., 1930, 52: 2060.
[368]
Adkins H, Cramer H I. J. Am. Chem. Soc., 1930, 52: 4349.
[369]
Buil M L, Esteruelas M A, Niembro S, Oliván M, Orzechowski L, Pelayo C, Vallribera A. Organometallics, 2010, 29: 4375.
[370]
Tomkins P, Gebauer-Henke E, Müller T E. ChemCatChem, 2016, 8: 546.
[371]
Gebauer-Henke E, Tomkins P, Leitner W, Müller T E. ChemCatChem, 2014, 6: 2910.
[372]
Murugesan K, Senthamarai T, Alshammari A S, Altamimi R M, Kreyenschulte C, Pohl M-M, Lund H, Jagadeesh R V, Beller M. ACS Catal., 2019, 9: 8581.
[373]
Quideau S, Pouységu L, Ozanne A, Gagnepain J. Molecules, 2005, 10: 201.
[374]
Giroux M A, Guérard K C, Beaulieu M A, Sabot C, Canesi S. Eur. J. Org. Chem., 2009, 2009: 3871.
[375]
Wang L, Fan R. Org. Lett., 2012, 14: 3596.
[376]
Wang L, Wang S E, Wang W, Fan R. RSC Adv., 2013, 3: 5775.
[377]
Bedford R B, Butts C P, Haddow M F, Osborne R, Sankey R F. Chem. Commun., 2009, 4832.
[378]
Cheng G, He X, Tian L, Chen J, Li C, Jia X, Li J. J. Org. Chem., 2015, 80: 11100.
[379]
Bouillon M E, Meyer H H. Tetrahedron, 2016, 72: 3151.
[380]
Liu S, Xu T, Liu Y, Wang Y. Angew. Chem. Int. Ed., 2024, 63: e202407841.
[381]
He Y, Qiu G. Org. Biomol. Chem., 2017, 15: 3485.
[382]
Huang K, Li J N, Qiu G, Xie W, Liu J B. RSC Adv., 2019, 9: 33460.
[383]
Chen Y, Chen Y J, Guan Z, He Y H. Tetrahedron, 2019, 75: 130763.
[384]
Chen Y, Lu F Y, Li R X, Guan Z, He Y H. Asian J. Org. Chem., 2021, 10: 668.
[385]
Wang Y, Liu J, Qiu G, Yang Y, Zhou H. Chinese J. Org. Chem., 2021, 41: 4798.
[386]
Zhang Y, Yang D, Lu D, Gong Y. Org. Lett., 2023, 25: 1320.
[387]
Kopach M E, Gonzalez J, Harman W D. J. Am. Chem. Soc., 1991, 113: 8972.
[388]
Gonzalez J, Sabat M, Harman W D. J. Am. Chem. Soc., 1993, 115: 8857.
[389]
Kolis S P, Gonzalez J, Bright L M, Harman W D. Organometallics, 1996, 15: 245.
[390]
Salomon R J, Todd M A, Sabat M, Myers W H, Harman W D. Organometallics, 2010, 29: 707.
[391]
(a) Wang W B, Lu S M, Yang P Y, Han X W, Zhou Y G. J. Am. Chem. Soc., 2003, 125: 10536.
(b) Lu S M, Han X W, Zhou Y G. Adv. Synth. Catal., 2004, 346: 909.
(c) Yang P Y, Zhou Y G. Tetrahedron: Asymmetry, 2004, 15: 1145.
(d) Wang D W, Wang X B, Wang D S, Lu S M, Zhou Y G, Li Y X. J. Org. Chem., 2009, 74: 2780.
(e) Gou F R, Li W, Zhang X, Liang Y M. Adv. Synth. Catal., 2010, 352: 244.
(f) Shi L, Ye Z S, Cao L L, Guo R N, Hu Y, Zhou Y G. Angew. Chem. Int. Ed., 2012, 51: 8286.
(g) Ye Z S, Chen M W, Chen Q A, Shi L, Duan Y, Zhou Y G. Angew. Chem. Int. Ed., 2012, 51: 10181.
(h) Iimuro A, Yamaji K, Kandula S, Nagano T, Kita Y, Mashima K. Angew. Chem. Int. Ed., 2013, 52: 2046.
(i) Ye Z S, Guo R N, Cai X F, Chen M W, Shi L, Zhou Y G. Angew. Chem. Int. Ed., 2013, 52: 3685.
(j) Chang M, Huang Y, Liu S, Chen Y, Krska S W, Davies I W, Zhang X. Angew. Chem. Int. Ed., 2014, 53: 1276.
(l) Huang W X, Yu C B, Ji Y, Liu L J, Zhou Y G. ACS Catal., 2016, 6: 2368.
(m) Ma W, Zhang J, Xu C, Chen F, He Y M, Fan Q H. Angew. Chem. Int. Ed., 2016, 55: 12891.
(n) Hu X H, Hu X P. Org. Lett., 2019, 21: 10003.
(o) Kim A N, Ngamnithiporn A, Welin E R, Daiger M T, Grünanger C U, Bartberger M D, Virgil S C, Stoltz B M. ACS Catal., 2020, 10: 3241.
(p) Li C, Pan Y, Feng Y, He Y M, Liu Y, Fan Q H. Org. Lett., 2020, 22: 6452.
(q) Han Z, Liu G, Yang X, Dong X Q, Zhang X. ACS Catal., 2021, 11: 7281.
(r) Wang L, Lin J, Xia C, Sun W. J. Org. Chem., 2021, 86: 16641.
[392]
(a) Zhou H, Li Z, Wang T, Wang L, Xu Y, He Q H, Pan J, Gu L, Chan A S C. Angew. Chem. Int. Ed., 2008, 47: 8464.
(b) Wang T L, Zhuo L G, Li Z W, Chen F, Ding Z Y, He Y M, Fan Q H, Xiang J F, Yu Z X, Chan A S C. J. Am. Chem. Soc., 2011, 133: 9878.
(c) Wang Z J, Zhou H F, Wang T L, He Y M, Fan Q H. Green Chem., 2009, 11: 767.
(d) Parekh V, Ramsden J A, Wills M. Tetrahedron: Asymmetry, 2010, 21: 1549.
(e) Chen Y, He Y M, Zhang S, Miao T, Fan Q H. Angew. Chem. Int. Ed., 2019, 58: 3809.
(f) Li C, Pan Y, Feng Y, He Y M, Liu L, Fan Q H. Org. Lett., 2020, 22: 6452.
(g) Ding Z Y, Wang T, He Y M, Chen F, Zhou H F, Fan Q H, Guo Q, Chan A S C. Adv. Synth. Catal., 2013, 355: 3727.
[393]
(a) Parekh V, Ramsden J A, Wills M. Tetrahedron: Asymmetry, 2010, 21: 1549.
(b) Wang C, Li C Q, Wu X F, Pettman A, Xiao J L. Angew. Chem. Int. Ed., 2009, 48: 6524.
(c) Wu J, Chen Z, Barnard J H, Gunasekar R, Pu C, Wu X, Zhang S, Ruan J, Xiao J. Nat. Catal., 2022, 5: 982.
[394]
(a) Glorius F, Spielkamp N, Holle S, Goddard R, Lehmann C W. Angew. Chem. Int. Ed., 2004, 43: 2850.
(b) Cai X F, Huang W X, Chen Z P, Zhou Y G. Chem. Commun., 2014, 50: 9588.
(c) Wagener T, Lückemeier L, Daniliuc C G, Glorius F. Angew. Chem. Int. Ed., 2021, 60: 6425.
[395]
(a) Liu C, Wang M, Liu S, Wang Y, Peng Y, Lan Y, Liu Q. Angew. Chem. Int. Ed., 2021, 60: 5108.
(b) Mao W, Song D, Guo J, Zhang K, Zheng C, Lin J, Huang L, Zheng L, Zhong W, Ling F. Green Chem., 2024, 26: 5933.
[396]
(a) Kubota K, Watanabe Y, Hayama K, Ito H. J. Am. Chem. Soc., 2016, 138: 4338.
(b) Yu H C, Islam S M, Mankad N P. ACS Catal., 2020, 10: 3670.
(c) Tamang S R, Singh A, Unruh D K, Findlater M. ACS Catal., 2018, 8: 6186.
(d) Liu J, Chen J Y, Jia M, Ming B, Jia J, Liao R Z, Tung C H, Wang W. ACS Catal., 2019, 9: 3849.
(e) Kaithal A, Chatterjee B, Gunanathan C. Org. Lett., 2016, 18: 3402.
(f) Behera D, Thiyagarajan S, Anjalikrishna P K, Suresh C H, Gunanathan C. ACS Catal., 2021, 11: 5885.
(g) Lortie J L, Dudding T, Gabidullin B M, Nikonov G I. ACS Catal., 2017, 7: 8454.
(h) Wang X, Zhang Y, Yuan D, Yao Y. Org. Lett., 2020, 22: 5695.
(i) Jeong J, Park S, Chang S. Chem. Sci., 2016, 7: 536.
(j) Zhang F, Song H, Zhuang X, Tung C H, Wang W. J. Am. Chem. Soc., 2017, 139: 17775.
(k) Liu X, Li B, Hua X, Cui D. Org. Lett. 2020, 22: 4960.
(l) Rodriguez J, Conley M P. Org. Lett., 2022, 24, 4680.
(m) Meher N K, Verma P K, Geetharani K. Org. Lett., 2023, 25: 87.
(n) Wang R, Kim D, Park S. ACS Catal., 2024, 14: 3582.
[397]
(a) Zhou Q, Zhang L, Meng W, Feng X, Yang J, Du H. Org. Lett., 2016, 18: 5189.
(b) Ma Y, Wang B, Zhang L, Hou Z. J. Am. Chem. Soc., 2016, 138: 3663.
(c) Ding F, Zhang Y, Zhao R, Jiang Y, Bao R L Y, Lin K, Shi L B. Chem. Commun., 2017, 53: 9262.
(d) Liu Z Y, Wen Z H, Wang X C. Angew. Chem., Int. Ed., 2017, 56: 5817.
(e) Clarke J J, Maekawa Y, Nambo M, Crudden C M. Org. Lett., 2021, 23: 6617.
(f) Yang Z Y, Luo H, Zhang M, Wang X C. ACS Catal., 2021, 11: 10824.
(g) Liu Z, Shi Z J, Liu L, Zhang M, Zhang M C, Guo H Y, Wang X C. J. Am. Chem. Soc., 2023, 145: 11789.
(h) Liu Z, He J H, Zhang M, Shi Z J, Tang H, Zhou X Y, Tian J J, Wang X C. J. Am. Chem. Soc., 2022, 144: 4810.
(i) Zhang M, Zhou Q, Luo H, Tang Z L, Xu X, Wang X C. Angew. Chem. Int. Ed., 2023, 62: e202216894
[398]
Oshima K, Ohmura T, Suginome M. J. Am. Chem. Soc., 2012, 134: 3699.
[399]
Rueping M, Antonchick A R, Theissmann T. Angew. Chem. Int. Ed., 2006, 45: 3683.
[400]
Wang D S, Chen Q A, Lu S M, Zhou Y G. Chem. Rev., 2012, 112: 2557.
[401]
Huang X Y, Zheng Q, Zou L M, Gu Q, Tu T, You S L. ACS Catal., 2022, 12: 4545.
[402]
(a) Sun Z, Yu S, Ding Z, Ma D. J. Am. Chem. Soc., 2007, 129: 9300.
(b) Kou X, Zhao Q, Guan Z H. Org. Chem. Front., 2020, 7: 829.
(c) He Q, Xie F, Xia C, Liang W, Guo Z, Zhu Z, Li Y, Chen X. Org. Lett., 2020, 22: 7976.
[403]
(a) Wang D, Jiang Y, Dong L, Li G, Sun B, Désau bry L, Yu P. J. Org. Chem., 2020, 85: 5027.
(b) Yan X, Ge L, Reis M C, Harutyunyan S R. J. Am. Chem. Soc., 2020, 142: 20247.
(c) Guo Y, Reis M C, Kootstra J, Harutyunyan S R. ACS Catal., 2021, 11, 8476.
(d) Knight B J, Tolchin Z A, Smith J M. Chem. Commun., 2021, 57: 2693.
(e) Grigolo T A, Subhit A R, Smith J M. Org. Lett., 2021, 23: 6703.
(f) McLaughlin C, Bitai J, Barber L J, Slawin A M Z, Smith A D. Chem. Sci., 2021, 12: 12001.
(g) Somprasong S, Reis M C, Harutyunyan S R. ACS Catal., 2024, 14: 13030.
[404]
Takamura M, Funabashi K, Kanai M, Shibasaki M. J. Am. Chem. Soc., 2001, 123: 6801.
[405]
(a) Zurro M, Asmus S, Bamberger J, Beckendorf S, Mancheño G O. Chem. Eur. J., 2016, 22: 3785.
(b) Duong Q N, Schifferer L, Mancheño G O. Eur. J. Org. Chem., 2019, 5452.
(c) Mengozzi L, Gualandi A, Cozzi P G. Eur. J. Org. Chem., 2016, 3200.
(d) Hirata G, Maeda H. Org. Lett., 2018, 20: 2853.
(e) Mancheño O G, Asmus S, Zurro M, Fischer T. Angew. Chem. Int. Ed., 2015, 54: 8823.
(f) Taylor M S, Tokunaga N, Jacobsen E N. Angew. Chem. Int. Ed., 2005, 44: 6700.
[406]
(a) Huang Y, Qi Z, Li X. Org. Lett., 2023, 25: 8439.
(b) Ortiz K G, Dotson J J, Robinson D J, Sigman M S, Karimov R R. J. Am. Chem. Soc., 2023, 145: 11781.
(c) Nadeau C, Aly S, Belyk K. J. Am. Chem. Soc., 2011, 133: 2878.
(d) Wang Y, Liu Y, Zhang D, Wei H, Shi M, Wang F. Angew. Chem. Int. Ed., 2016, 55: 3776.
(e) Robinson D J, Spurlin S P, Gorden J D, Karimov R R. ACS Catal., 2020, 10: 51.
(f) Robinson D J, Ortiz K G, O’Hare N P, Karimov R R. Org. Lett., 2022, 24: 3445.
[407]
(a) Bertuzzi G, Sinisi A, Caruana L, Mazzanti A, Fochi M, Bernardi L. ACS Catal., 2016, 6: 6473.
(b) Zhang M, Sun W, Zhu G, Bao G, Zhang B, Hong L, Li M, Wang R. ACS Catal., 2016, 6: 5290.
(c) Cai Y, Gu Q, You S L. Org. Biomol. Chem., 2018, 16: 6146.
[408]
(a) Gao Z, Guo Y. Chem. Commun., 2022, 58: 9393.
(b) Fischer T, Duong Q N, Mancheño O G. Chem. Eur. J., 2017, 23: 5983.
(c) Choudhury A R, Mukherjee S. Chem. Sci., 2016, 7: 6940.
[409]
Shao W, Wang Y, Yang Z P, Zhang X, You S L. Chem. Asian. J., 2018, 13: 1103.
[410]
(a) Zhang X, Yang Z P, Huang L, You S L. Angew. Chem. Int. Ed., 2015, 54: 1873.
(b) Li C, Breit B. Chem. Eur. J., 2016, 22: 14655.
(c) Tu H F, Yang P, Lin Z H, Zheng C, You S L. Nat. Chem., 2020, 12: 838.
(d) Wang Y, Xu Y, Khan S, Zhang Z, Khan A. New J. Chem., 2022, 46: 11138.
(e) Tu H F, Nie Y H, Zheng C, You S L. Adv. Synth. Catal., 2022, 364: 3432.
(f) Yang Z P, Jiang R, Zheng C, You S L. J. Am. Chem. Soc., 2018, 140: 3114.
[411]
(a) Wu Y C, Jhong Y, Lin H J, Swain S P, Tsai H H G, Hou D R. Adv. Synth. Catal., 2019, 361: 4966.
[412]
Lee S, Diab S, Queval P, Sebban M, Chataigner I, Piettre S R. Chem. Eur. J., 2013, 19: 7181.
[413]
Bastrakov M A, Kucherova A Y, Fedorenko A K, Starosotnikov A M, Fedyanin I V, Dalinger I L, Shevelev S A. Arkivoc, 2017, 181.
[414]
Bastrakov S A, Fedorenko A K, Starosotnikov A M, Kachala V V, Shevelev S A. Chem. Heterocycl. Compd., 2019, 55: 72.
[415]
Xiong Q, Dong S X, Chen Y, Liu X H, Feng X M. Nat. Commun., 2019, 10: 2116.
[416]
Day J, McKeever-Abbas B, Dowden J. Angew. Chem., Int. Ed., 2016, 55: 5809.
[417]
Yuan C H, Wu Y, Wang D Q, Zhang Z H, Wang C, Zhou L J, Zhang C, Song B A, Guo H C. Adv. Synth. Catal., 2018, 360: 652.
[418]
Lee J Y, Varshnaya R K, Yoo E J. Org. Lett., 2022, 24: 3731.
[419]
Preindl J, Chakrabarty S, Waser J. Chem. Sci., 2017, 8: 7112.
[420]
Yang Y, Xu C H, Teng F, Li J H. Adv. Synth. Catal., 2020, 362: 3369.
[421]
Jin Y, Ou L, Yang H, Fu H. J. Am. Chem. Soc., 2017, 139: 14237.
[422]
Leitch J A, Rogova T, Duarte F, Dixon D J. Angew. Chem. Int. Ed., 2020, 59: 4121.
[423]
Ji P, Davies C C, Gao F, Chen J, Meng X, Houk K N, Chen S, Wang W. Nat. Commun., 2022, 13: 4565.
[424]
Chatterjee A, Koenig B. Angew. Chem. Int. Ed., 2019, 58: 14289.
[425]
Wertjes W C, Okumura M, Sarlah D. J. Am. Chem. Soc., 2019, 141: 163.
[426]
Southgate E H, Pospech J, Fu J, Holycross D R, Sarlah D. Nat. Chem., 2016, 8: 922.
[427]
Siddiqi Z, Bingham T W, Shimakawa T, Hesp, K D, Shavnya A, Sarlah D. J. Am. Chem. Soc., 2024, 146: 2358.
[428]
Ma J J, Strieth-Kalthoff F, Dalton T, Freitag M, Schwarz J L, Bergander K, Daniliuc C, Glorius F. Chem, 2019, 5: 2854.
[429]
Ma J, Chen S M, Bellotti P, Guo R Y, Schafer F, Heusler A, Zhang X, Daniliuc C, Brown M K, Houk K N, Glorius F. Science, 2021, 371: 1338.
[430]
Guo R Y, Adak S, Bellotti P, Gao X F, Smith W W, Le S N, Ma J J, Houk K N, Glorius F, Chen S M, Brown M K. J. Am. Chem. Soc., 2022, 144: 17680.
[431]
Kleinmans R, Dutta S, Ozols K, Shao H L, Schafer F, Thielemann R E, Chan H T, Daniliuc C G, Houk K N, Glorius F. J. Am. Chem. Soc., 2023, 145: 12324.
[432]
Wertjes W C, Southgate E H, Sarlah D. Chem. Soc. Rev., 2018, 47: 7996.
[433]
Sharma U K, Ranjan P, Van der Eycken E V, You S L. Chem. Soc. Rev., 2020, 49: 8721.
[434]
Zheng C, You S L. ACS Cent. Sci., 2021, 7: 432.
[435]
Wiesenfeldt M P, Nairoukh Z, Li W, Glorius F. Science, 2017, 357: 908.
[436]
Kuwano R, Morioka R, Kashiwabara M, Kameyama N. Angew. Chem. Int. Ed., 2012, 51: 4136.
[437]
Wiesenfeldt M P, Nairoukh Z, Dalton T, Glorius F. Angew. Chem. Int. Ed., 2019, 58: 10460.
[438]
Qiu J Y, Zeng W L, Xie H, Wang M Y, Li W. Angew. Chem. Int. Ed. 2023, 62, e202218961.
[439]
Zhang J, Mück Lichtenfeld C, Studer A. Nature, 2023, 619: 506.
[440]
Liu D H, Ma J. Angew. Chem. Int. Ed., 2024, 63, e202402819.
[441]
Yuan T, Sun L, Wu Z, Wang R, Cai X, Lin W, Zheng M, Wang X. Nat. Catal. 2022, 5: 1157.
[442]
Cole J P, Chen D F, Kudisch M, Pearson R M, Lim C H, Miyake G M. J. Am. Chem. Soc., 2020, 142: 13573.
[443]
Tan E Y K, Mat Lani A S, Sow W, Liu Y, Li H, Chiba S. Angew. Chem. Int. Ed., 2023, 62: e202309764.
[444]
Peters B K, Rodriguez K X, Reisberg S H, Beil S B, Hickey D P, Kawamata Y, Collins M, Starr J, Chen L, Udyavara S, Klunder K, Gorey T J, Anderson S L, Neurock M, Minteer S D, Baran P S. Science, 2019, 363: 838.
[445]
Hudlicky T, Reed J W. Chem. Soc. Rev., 2009, 38: 3117.
[446]
Choukairi Afailal N, Borrell M, Cianfanelli M, Costas M. J. Am. Chem. Soc., 2024, 146: 240.
[447]
Meyers A I. J. Org. Chem., 2005, 70: 6137.
[448]
Liu L, Wang Z, Zhao F, Xi Z. J. Org. Chem., 2007, 72: 3484.
[449]
Lee S, Chataigner I, Piettre S R. Angew. Chem. Int. Ed., 2011, 50: 472.
[450]
Lee S, Diab S, Queval P, Sebban M, Chataigner I, Piettre S R. Chem. Eur. J., 2013, 19: 7181.
[451]
Trost B M, Ehmke V, O’Keefe B M, Bringley D A. J. Am. Chem. Soc., 2014, 136: 8213.
[452]
Kündig E P, Ripa A, Bernardinelli G. Angew. Chem. Int. Ed., 1992, 31: 1071.
[453]
Price D A, Simpkins N S, MacLeod A M, Watt A P. J. Org. Chem., 1994, 59: 1961.
[454]
Quattropani A, Anderson G, Bernardinelli G, Kündig E P. J. Am. Chem. Soc., 1997, 119: 4773.
[455]
Amurrio D, Khan K, Kündig E P. J. Org. Chem., 1996, 61: 2258.
[456]
(a) Wang M Y, Zeng W L, Chen L, Yuan Y F, Li W. Angew. Chem. Int. Ed., 2024, 136: e202403917.
(b) Li C Q, Jiang X, Wang M Y, Zeng W L, Li W. CCS Chem., 2024, 6: 2066.
(c) Li Z J, Wang M Y, Li C Q, Zeng W L, Li W. Chem. Eur. J., 2023, 29: e202300776.
[457]
Pigge F C, Coniglio J J, Dalvi R. J. Am. Chem. Soc., 2006, 128: 3498.
[458]
Pigge F C, Dhanya R, Hoefgen E R. Angew. Chem. Int. Ed., 2007, 46: 2887.
[459]
Pigge F C, Dalvi R. Tetrahedron, 2008, 64: 10123.
[460]
Bao M, Nakamura H, Yamamoto Y. J. Am. Chem. Soc., 2001, 123: 759.
[461]
Mendis S N, Tunge J A. Chem. Commun., 2016, 52: 7695.
[462]
Jacquemot G, Ménard M A, L'Homme C, Canesi S. Chem. Sci., 2013, 4: 1287.
[463]
Liu S, Xu T, Liu Y, Wang Y. Angew. Chem. Int. Ed., 2024, 63: e202407841.
[464]
Li K, Huang S, Liu T, Jia S, Yan H. J. Am. Chem. Soc., 2022, 144: 7374.
[465]
Tyler J L, Noble A, Aggarwal V K. Angew. Chem. Int. Ed., 2022, 134: e202114235.
[466]
Liebov B K, Harman W D. Chem. Rev., 2017, 117: 13721.
[467]
Lankenau A W, Iovan D A, Pienkos J A, Salomon R J, Wang S, Harrison D P, Myers W H, Harman W D. J. Am. Chem. Soc., 2015, 137: 3649.
[468]
Wilson K B, Myers J T, Nedzbala H S, Combee L A, Sabat M, Harman W D. J. Am. Chem. Soc., 2017, 139: 11401.
[469]
Smith J A, Wilson K B, Sonstrom R E, Kelleher P J, Welch K D, Pert E K, Westendorff K S, Dickie D A, Wang X, Pate B H, Harman W D. Nature, 2020, 581: 288.
[470]
Simpson S R, Siano P, Siela D J, Diment L A, Song B C, Westendorff K S, Ericson M N, Welch K D, Dickie D A, Harman W D. J. Am. Chem. Soc., 2022, 144: 9489.
[471]
Chen W, Bai J, Zhang G. Adv. Synth. Catal., 2017, 359: 1227.
[472]
Zhou B, Wang H, Cao Z Y, Zhu J W, Liang R X, Hong X, Jia Y X. Nat. Commun., 2020, 11: 4380.
[473]
Wefelscheid U K, Berndt M, Reißig H U. Eur. J. Org. Chem., 2008, 3635.
[474]
Wang Y, Zhang W Y, Yu Z L, Zheng C, You S L. Nat. Synth., 2022, 1: 401.
[475]
Cheng Y Z, Feng Z L J, Zhang X, You S L. Chem. Soc. Rev., 2022, 51: 2145.
[476]
Gao F, Yang C, Gao G Y, Xia W J. Org. Lett., 2015, 17: 3478.
[477]
Soni V K, Hwang H S, Moon Y K, Park S W, You Y, Cho E J. J. Am. Chem. Soc., 2019, 141: 10538.
[478]
Li H J, Subbotina E, Bunrit A, Wang F, Samec J S M. Chem. Sci., 2019, 10: 3681.
[479]
Cheng Y Z, Huang X L, Zhuang W H, Zhao Q R, Zhang X, Mei T S, You S L. Angew. Chem. Int. Ed., 2020, 59: 18062.
[480]
Gao Y, Wang H, Chi Z, Yang L, Zhou C, Li G. CCS Chem., 2022, 4: 1565.
[481]
Yuan P F, Huang X T, Long L, Huang T, Sun C L, Yu W, Wu L Z, Chen H, Liu Q. Angew. Chem. Int. Ed., 2024, 63: e202317968.
[482]
Remy R, Bochet C G. Chem. Rev., 2016, 116: 9816.
[483]
Scharf H D, Leismann H, Erb W, Üaidetzka H W, Aretz J. Pure Appl. Chem., 1975, 41: 581.
[484]
Kishikawa K, Akimoto S, Kohmoto S, Yamamoto M, Yamada K. J. Chem. Soc., Perkin Trans. 1, 1997, 77.
[485]
Kohmoto S, Miyaji Y, Tsuruoka M, Kishikawa K, Yamamoto M, Yamada K. J. Chem. Soc., Perkin Trans. 1, 2001, 2082.
[486]
Rai P, Maji K, Jana S K, Maji B. Chem. Sci., 2022, 13: 12503.
[487]
Wang W, Cai Y, Guo R, Brown M K. Chem. Sci., 2022, 13: 13582.
[488]
Zhen G, Zeng G, Wang F, Cao X, Yin B. Adv. Synth. Catal., 2023, 365: 43.
[489]
Chiminelli M, Serafino A, Ruggeri D, Marchiò L, Bigi F, Maggi R, Malacria M, Maestri G. Angew. Chem. Int. Ed., 2023, 62: e202216817.
[490]
Southgate E H, Pospech J, Fu J, Holycross D R, Sarlah D. Nat. Chem., 2016, 8: 922.
[491]
Okumura M, Nakamata Huynh S M, Pospech J, Sarlah D. Angew. Chem. Int. Ed., 2016, 55: 15910.
[492]
Okumura M, Shved A S, Sarlah D. J. Am. Chem. Soc., 2017, 139: 17787.
[493]
Hernandez L W, Klöckner U, Pospech J, Hauss L, Sarlah D. J. Am. Chem. Soc., 2018, 140: 4503.
[494]
Wertjes W C, Okumura M, Sarlah D. J. Am. Chem. Soc., 2019, 141: 163.
[495]
Tang C, Okumura M, Zhu Y, Hooper A R, Zhou Y, Lee Y H, Sarlah D. Angew. Chem. Int. Ed., 2019, 58: 10245.
[496]
Tang C, Okumura M, Deng H, Sarlah D. Angew. Chem. Int. Ed., 2019, 58: 15762.
[497]
Siddiqi Z, Wertjes W C, Sarlah D. J. Am. Chem. Soc., 2020, 142: 10125.
[498]
Piacentini P, Bingham T W, Sarlah D. Angew. Chem. Int. Ed., 2022, 61, e202208014.
[499]
Ikeda K, Kojima R, Kawai K, Murakami T, Kikuchi T, Kojima M, Yoshino T, Matsunaga S. J. Am. Chem. Soc., 2023, 145: 9326.
[500]
Li M, Huang X L, Zhang Z Y, Wang Z, Wu Z, Yang H, Shen W J, Cheng Y Z, You S L. J. Am. Chem. Soc., 2024, 146: 16982.
[501]
Pradhan S, Mohammadi F, Bouffard J. J. Am. Chem. Soc., 2023, 145: 12214.
[502]
Reisman S E, Nani R R, Levin S. Synlett, 2011, 2437.
[503]
Smith K L, Padgett C L, Mackay W D, Johnson J S. J. Am. Chem. Soc., 2020, 142: 6449.
[504]
Ito T, Harada S, Homma H, Takenaka H, Hirose S, Nemoto T. J. Am. Chem. Soc., 2021, 143: 604.
[505]
Cheng Z, Xu H, Hu Z, Zhu M, Houk K N, Xue X S, Jiao N. J. Am. Chem. Soc., 2024, 146: 16963.
[506]
Zhao W, Huang X, Zhan Y, Zhang Q, Li D, Zhang Y, Kong L, Peng B. Angew. Chem. Int. Ed., 2019, 58: 17210.
[507]
Alshreimi A S, Zhang G, Reidl T W, Peña R L, Koto N G, Islam S M, Wink D J, Anderson L L. Angew. Chem. Int. Ed., 2020, 59: 15244.
[508]
Chen P F, Zhou B, Wu P, Wang B, Ye L W. Angew. Chem. Int. Ed., 2021, 60: 27164.
[509]
Shi Q, Liao Z, Liu Z, Wen J, Li C, He J, Deng J, Cen S, Cao T, Zhou J, Zhu S. Nat. Commun., 2022, 13: 4402.
[510]
Wang D C, Xie M S, Guo H M, You S L. Angew. Chem. Int. Ed., 2016, 55: 14111.
[511]
Zhang M C, Wang D C, Xie M S, Qu G R, Guo H M, You S L. Chem, 2019, 5: 156.
[512]
Wang Z H, Zhang H H, Wang D M, Xu P F, Luo Y C. Chem. Commun., 2017, 53: 8521.
[513]
Singh R R, Skaria M, Chen L Y, Cheng M J, Liu R S. Chem. Sci., 2019, 10: 1201.
[514]
Cheng Q, Xie J H, Weng Y C, You S L. Angew. Chem. Int. Ed., 2019, 58: 5739.
[515]
Schlepphorst C, Wiesenfeldt M P, Glorius F. Chem. Eur. J., 2018, 24: 356.
[516]
Wan Q, Zheng C, Yuan Y F, You S L. Sci. Bull., 2022, 67: 1688.
[517]
Zhang S S, Wang R X, Gu Q, You S L. CCS Chem., 2024, DOI: doi.org/10.31635/ccschem.024.202403981.
[518]
Yang Z P, Zheng C, Huang L, Qian C, You S L. Angew. Chem. Int. Ed., 2017, 56: 1530.
[519]
Greenhalgh M D, Qu S, Slawin A M Z, Smith A D. Chem. Sci., 2018, 9: 4909.
[520]
Chu Y P, Hu F, Feng P, Hui X P. Org. Chem. Front., 2022, 9: 1556.
[521]
Marta Velázquez M, Fernández R, Lassaletta J M, Monge D. Org. Lett., 2023, 25: 8797.
[522]
Ketelboeter D R, Pappoppula M, Aponick A. J. Am. Chem. Soc., 2024, 146: 11610.
[523]
Xu N, Peng X Q, Chen Z, Song S J, Li J J. ACS Sustain. Chem. Eng., 2023, 11: 13142.
[524]
Manning J R, Davies H M L. Tetrahedron, 2008, 64: 6901.
[525]
Li L X, Ning Y Q, Chen H Z, Ning Y Y, Sivaguru P, Liao P Q, Zhu Q W, Ji Y, Ruiter G D, Bi X H. Angew. Chem. Int. Ed., 2024, 63, e202313807.
[526]
Jadhav P D, Lu X, Liu R S. ACS Catal., 2018, 8: 9697.
[527]
Xu W, Zhao J D, Li X D, Liu Y H. J. Org. Chem., 2018, 83: 15470.

Funding

National Natural Science Foundation of China(22031012)
PDF(31989 KB)

Accesses

Citation

Detail

Sections
Recommended

/