Oxidation Carbonylation Reaction of Terminal Alkynes with Carbon Monoxide/Oxygen

Rong Fan; Yajing Li; Xiaona Hu; Ruiqi Zhang; Xi Liu; Dongshun Zhang; Zhuo Yi

doi:10.7536/PC240327

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Prog Chem ›› 2024, Vol. 36 ›› Issue (12) : 1944-1955. DOI: 10.7536/PC240327

Review

Oxidation Carbonylation Reaction of Terminal Alkynes with Carbon Monoxide/Oxygen

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Abstract

Oxidative carbonylation reactions are powerful methodologies for producing carbonyl derivatives, which show advantages such as wide source of raw materials and a diverse range of products. In recent years, with the concept of environmental protection deeply rooted, developing efficient and green oxidative carbonylation reactions with carbon monoxide and oxygen as reactants, attracts much interest in this field. The C(sp)-H bonds of terminal alkynes exhibit excellent reactivity in oxidative carbonylation reactions, which could form a series of unsaturated carbonyl compounds. This review introduces the oxidative carbonylation reactions of terminal alkynes and their applications in total synthesis, including oxidative alkoxycarbonylation, oxidative aminocarbonylation, and oxidative carbonylation-cyclization, with the focus on the reaction mechanism of carbonylation and metal oxidation. Finally, the future development trends of this field are prospected.

Contents

1 Introduction

2 Oxidative alkoxycarbonylation

3 Oxidative aminocarbonylation

4 Oxidative carbonylation-cyclization

5 Application of oxidative carbonylation in total synthesis

6 Conclusion and outlook

Key words

terminal alkynes / carbon monoxide / oxygen / oxidative alkoxycarbonylation / oxidative aminocarbonylation

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Rong Fan , Yajing Li , Xiaona Hu , et al . Oxidation Carbonylation Reaction of Terminal Alkynes with Carbon Monoxide/Oxygen[J]. Progress in Chemistry. 2024, 36(12): 1944-1955 https://doi.org/10.7536/PC240327

References

List( Publishing order | Descend order by publishing year | Descend order by cited within ) Chart analysis

[1]	Peng J B, Geng H Q, Wu X F. Chem, 2019, 5(3): 526. Cited in this article [1]

[2]	Wang P, Liu H, Yang D. Chem. J. Chinese Universities, 2021, 42(10): 3024. (王鹏, 刘欢, 杨妲. 高等学校化学学报, 2021, 42(10): 3024.). Cited in this article [1]

[3]	Tian Q Q, Yin X, Sun R J, Wu X F, Li Y H. Coord. Chem. Rev., 2023, 475: 214900. Cited in this article [1]

[4]	Shi F, Wang H, Dai X. Carbonyl Compounds: Reactants, Catalysts and Products. Weinheim: Wiley-VCH, 2021. 1. Cited in this article [1]

[5]	Liu Q, Zhang H, Lei A W. Angew. Chem. Int. Ed., 2011, 50(46): 10788. Cited in this article [1]

[6]	Cheng L J, Mankad N P. Acc. Chem. Res., 2021, 54(9): 2261. Cited in this article [1]

[7]	Ang W J, Lo L C, Lam Y. Tetrahedron, 2014, 70(45): 8545. Cited in this article [1]

[8]	Xu J X, Kuai C S, Chen B, Wu X F. Chem Catal., 2022, 2(3): 477. Cited in this article [1]

[9]	Zhao F, Ai H J, Wu X F. Angew. Chem. Int. Ed., 2022, 61(17): e202200062. Cited in this article [1]

[10]	Wu X F, Neumann H, Beller M. Chem. Rev., 2013, 113(1): 1. Cited in this article [1]

[11]	Das D, Bhanage B M. Adv. Synth. Catal., 2020, 362(15): 3022. Cited in this article [1]

[12]	Rowley J M, Lobkovsky E B, Coates G W. J. Am. Chem. Soc., 2007, 129(16): 4948. Cited in this article [1]

[13]	Hubbell A K, LaPointe A M, Lamb J R, Coates G W. J. Am. Chem. Soc., 2019, 141(6): 2474. Cited in this article [1]

[14]	Xu J X, Wu X F. J. Org. Chem., 2019, 84(16): 9907. Cited in this article [1]

[15]	Fan Q J, Liu J H, Chen J, Xia C G. Chin. J. Catal., 2012, 33(9): 1435. (樊启佳, 刘建华, 陈静, 夏春谷. 催化学报, 2012, 33(9): 1435.). Cited in this article [1]

[16]	Yang J, Liu J W, Neumann H, Franke R, Jackstell R, Beller M. Science, 2019, 366(6472): 1514. Cited in this article [1]

[17]	Zhang Y, Sigrist M, Dydio P. Eur. J. Org. Chem., 2021, 2021(44): 5985. Cited in this article [1]

[18]	Wang P, Yang D, Liu H, Chin. J. Org. Chem., 2021, 41(9): 3379. (王鹏, 杨妲, 刘欢. 有机化学, 2021, 41(9): 3379.). Cited in this article [1]

[19]	Peng J B. Adv. Synth. Catal., 2020, 362(15): 3059. Cited in this article [1]

[20]	Zhang S K, Neumann H, Beller M. Chem. Soc. Rev., 2020, 49(10): 3187. Cited in this article [1]

[21]	Liu Y C, Chen Y H, Yi H, Lei A W. ACS Catal., 2022, 12(13): 7470. Cited in this article [1]

[22]	Lukasevics L, Grigorjeva L. Org. Biomol. Chem., 2020, 18(38): 7460. Cited in this article [1]

[23]	Zhu C, Liu J, Li M B, Bäckvall J E. Chem. Soc. Rev., 2020, 49(2): 341. Cited in this article [1]

[24]	Lukasevics L, Cizikovs A, Grigorjeva L. Org. Lett., 2021, 23(7): 2748. Cited in this article [1]

[25]	Liang Z J, Zhang J T, Liu Z X, Wang K, Zhang Y H. Tetrahedron, 2013, 69(31): 6519. Cited in this article [1]

[26]	Houlden C E, Hutchby M, Bailey C D, Ford J G, Tyler S N G, Gagné M R, Lloyd-Jones G C, Booker-Milburn K I. Angew. Chem. Int. Ed., 2009, 48(10): 1830. Cited in this article [1]

[27]	Chen H J, Cai C B, Liu X H, Li X W, Jiang H F. Chem. Commun., 2011, 47(44): 12224. Cited in this article [1]

[28]	Qiu Y A, Yang B, Jiang T, Zhu C, Bäckvall J E. Angew. Chem. Int. Ed., 2017, 56(12): 3221. Cited in this article [1]

[29]	Yoo E J, Wasa M, Yu J Q. J. Am. Chem. Soc., 2010, 132(49): 17378. Cited in this article [1]

[30]	Li M B, Inge K A, Posevins D, Gustafson K P J, Qiu Y A, Bäckvall J E. J. Am. Chem. Soc., 2018, 140(44): 14604. Cited in this article [1]

[31]	Giri R, Yu J Q. J. Am. Chem. Soc., 2008, 130(43): 14082. Cited in this article [1]

[32]	Liang D D, He Y M, Zhu Q. Org. Lett., 2014, 16(10): 2748. Cited in this article [1]

[33]	Li H, Cai G X, Shi Z J. Dalton Trans., 2010, 39(43): 10442. Cited in this article [1]

[34]	Liu B, Jiang H Z, Shi B F. Org. Biomol. Chem., 2014, 12(16): 2538. Cited in this article [1]

[35]	Wang C, Zhang L, Chen C P, Han J, Yao Y M, Zhao Y S. Chem. Sci., 2015, 6(8): 4610. Cited in this article [1]

[36]	Zhao M N, Ran L F, Chen M, Ren Z H, Wang Y Y, Guan Z H. ACS Catal., 2015, 5(2): 1210. Cited in this article [1]

[37]	Zeng L, Li H R, Hu J C, Zhang D C, Hu J Y, Peng P, Wang S C, Shi R Y, Peng J Q, Pao C W, Chen J L, Lee J F, Zhang H, Chen Y H, Lei A W. Nat. Catal., 2020, 3(5): 438. Cited in this article [1]

[38]	Wu Y, Zeng L, Li H R, Cao Y, Hu J C, Xu M H, Shi R Y, Yi H, Lei A W. J. Am. Chem. Soc., 2021, 143(32): 12460. Cited in this article [1]

[39]	Shi Y R, Xia C G, Huang Y, He L. Chem. Asian J., 2021, 16(19): 2830. Cited in this article [1]

[40]	Zeng L, Li H R, Tang S, Gao X L, Deng Y, Zhang G T, Pao C W, Chen J L, Lee J F, Lei A W. ACS Catal., 2018, 8(6): 5448. Cited in this article [1]

[41]	Luo X H, Wang G Q, Yuan B, Gao T. Chem. Eng. Management, 2021, (03): 125. (罗小会, 汪钢强, 袁兵, 高涛. 化工管理, 2021, (03): 125.). Cited in this article [1]

[42]	He W M. Modern Chem. Res., 2019, (01): 1. (何卫民. 当代化工研究, 2019, (01): 1.). Cited in this article [1]

[43]	Liao Y, Liu F, Shi Z J. Chem. Commun., 2021, 57(98): 13288. Cited in this article [1]

[44]	Lei J, Su L B, Zeng K, Chen T Q, Qiu R H, Zhou Y B, Au C T, Yin S F. Chem. Eng. Sci., 2017, 171: 404. Cited in this article [2]

[45]	Chinchilla R, Nájera C. Chem. Soc. Rev., 2011, 40(10): 5084. Cited in this article [2]

[46]	Li J X, He D, Lin Z D, Wu W Q, Jiang H F. Org. Chem. Front., 2021, 8(13): 3502. Cited in this article [1]

[47]	Mohajer F, Heravi M M, Zadsirjan V, Poormohammad N. RSC Adv., 2021, 11(12): 6885. Cited in this article [1]

[48]	Liu N, Zhou L, Wu Z Q. Acc. Chem. Res., 2021, 54(20): 3953. Cited in this article [1]

[49]	Liu B, Shi B F. Synlett, 2013, 24(17): 2274. Cited in this article [1]

[50]	Zhang H, Liu D, Chen C Y, Liu C, Lei A W. Chem. - Eur. J., 2011, 17(35): 9581. Cited in this article [1]

[51]	Shi R Y, Lu L J, Zhang H, Chen B R, Sha Y C, Liu C, Lei A W. Angew. Chem. Int. Ed., 2013, 52(40): 10582. Cited in this article [1]

[52]	Zhang X P, Dong S X, Niu X L, Li Z W, Fan X S, Zhang G S. Org. Lett., 2016, 18(18): 4634. Cited in this article [1]

[53]	Tsuji J, Takahashi M, Takahashi T. Tetrahedron Lett., 1980, 21(9): 849. Cited in this article [1]

[54]	Zung T T, Bruk L G, Temkin O N. Mendeleev Commun., 1994, 4(1): 2. Cited in this article [1]

[55]	Sakurai Y, Sakaguchi S, Ishii Y. Tetrahedron Lett., 1999, 40(9): 1701. Cited in this article [1]

[56]	Zargarian D, Alper H. Organometallics, 1991, 10(8): 2914. Cited in this article [1]

[57]	Giannoccaro P, Aresta M, Doronzo S, Ferragina C. Appl. Organometal. Chem., 2000, 14(10): 581. Cited in this article [1]

[58]	Izawa Y, Shimizu I, Yamamoto A. Bull. Chem. Soc. Jpn., 2004, 77(11): 2033. Cited in this article [1]

[59]	Tereniak S J, Landis C R, Stahl S S. ACS Catal., 2018, 8(4): 3708. Cited in this article [1]

[60]	Izawa Y, Shimizu I, Yamamoto A. Chem. Lett., 2005, 34(7): 1060. Cited in this article [1]

[61]	Gadge S T, Bhanage B M. Synlett, 2013, 24(8): 981. Cited in this article [1]

[62]	Cao Q, Hughes N L, Muldoon M J. Chem. - Eur. J., 2016, 22(34): 11982. Cited in this article [1]

[63]	Gabriele B, Salerno G, Veltri L, Costa M. J. Organomet. Chem., 2001, 622(1-2): 84. Cited in this article [1]

[64]	Kolekar Y A, Bhanage B M. New J. Chem., 2022, 46(30): 14421. Cited in this article [1]

[65]	Khedkar M V, Tambade P J, Qureshi Z S, Bhanage B M. Eur. J. Org. Chem., 2010, 2010(36): 6981. Cited in this article [1]

[66]	Tambade P J, Patil Y P, Panda A G, Bhanage B M. Eur. J. Org. Chem., 2009, 2009(18): 3022. Cited in this article [1]

[67]	Gadge S T, Khedkar M V, Lanke S R, Bhanage B M. Adv. Synth. Catal., 2012, 354(10): 2049. Cited in this article [1]

[68]	Mane R S, Bhanage B M. J. Org. Chem., 2016, 81(12): 4974. Cited in this article [1]

[69]	Hopkinson M N, Richter C, Schedler M, Glorius F. Nature, 2014, 510: 485. Cited in this article [1]

[70]	Bellotti P, Koy M, Hopkinson M N, Glorius F. Nat. Rev. Chem., 2021, 5(10): 711. Cited in this article [1]

[71]	Enders D, Niemeier O, Henseler A. Chem. Rev., 2007, 107(12): 5606. Cited in this article [1]

[72]	Que Y L, He H B. Eur. J. Org. Chem., 2020, 2020(37): 5917. Cited in this article [1]

[73]	Ishii T, Nagao K, Ohmiya H. Chem. Sci., 2020, 11(22): 5630. Cited in this article [1]

[74]	Zhang C H, Hooper J F, Lupton D W. ACS Catal., 2017, 7(4): 2583. Cited in this article [1]

[75]	Zhang C Y, Liu J H, Xia C G. Catal. Sci. Technol., 2015, 5(10): 4750. Cited in this article [1]

[76]	Hughes N L, Brown C L, Irwin A A, Cao Q, Muldoon M J. ChemSusChem, 2017, 10(4): 675. Cited in this article [1]

[77]	Ziccarelli I, Mancuso R, Giacalone F, Calabrese C, La Parola V, De Salvo A, Della Ca N, Gruttadauria M, Gabriele B. J. Catal., 2022, 413: 1098. Cited in this article [1]

[78]	Sang R, Hu Y Y, Razzaq R, Jackstell R, Franke R, Beller M. Org. Chem. Front., 2021, 8(4): 799. Cited in this article [1]

[79]	Wang P, Wang Y X, Neumann H, Beller M. Chem. Sci., 2022, 13(45): 13459. Cited in this article [1]

[80]	Yang J, Wang P, Neumann H, Jackstell R, Beller M. Ind. Chem. Mater., 2023, 1(2): 155. Cited in this article [1]

[81]	Yang J, Liu J W, Jackstell R, Beller M. Chem. Commun., 2018, 54(76): 10710. Cited in this article [1]

[82]	Gabriele B, Costa M, Salerno G, Chiusoli G P. J. Chem. Soc., hem. Commun., 1994(12): 1429. Cited in this article [2]

[83]	Gabriele B, Salerno G, De Pascali F, Costa M, Chiusoli G P. J. Chem. Soc., erkin Trans. 1, 1997(2): 147. Cited in this article [1]

[84]	Bonardi A, Costa M, Gabriele B, Salerno G, Chiusoli G P. Tetrahedron Lett., 1995, 36(41): 7495. Cited in this article [1]

[85]	Gabriele B, Salerno G, De Pascali F, Scianò G T, Costa M, Chiusoli G P. Tetrahedron Lett., 1997, 38(39): 6877. Cited in this article [1]

[86]	Gabriele B, Salerno G, Plastina P, Costa M, Crispini A. Adv. Synth. Catal., 2004, 346(2-3): 351. Cited in this article [1]

[87]	Gabriele B, Plastina P, Salerno G, Mancuso R, Costa M. Org. Lett., 2007, 9(17): 3319. Cited in this article [1]

[88]	Bacchi A, Costa M, Gabriele B, Pelizzi G, Salerno G. J. Org. Chem., 2002, 67(13): 4450. Cited in this article [1]

[89]	Gabriele B, Salerno G, Veltri L, Costa M, Massera C. Eur. J. Org. Chem., 2001, 2001(24): 4607. Cited in this article [1]

[90]	Mancuso R, Raut D S, Marino N, De Luca G, Giordano C, Catalano S, Barone I, Andò S, Gabriele B. Chem. - Eur. J., 2016, 22(9): 3053. Cited in this article [1]

[91]	Gabriele B, Salerno G, Plastina P. Lett. Org. Chem., 2004, 1(2): 134. Cited in this article [1]

[92]	Veltri L, Giofrè S V, Devo P, Romeo R, Dobbs A P, Gabriele B. J. Org. Chem., 2018, 83(3): 1680. Cited in this article [1]

[93]	Veltri L, Russo P, Prestia T, Vitale P, Romeo R, Gabriele B. J. Catal., 2020, 386: 53. Cited in this article [1]

[94]	Ma K Q, Martin B S, Yin X L, Dai M J. Nat. Prod. Rep., 2019, 36(1): 174. Cited in this article [1]

[95]	Sessions E H, O’Connor R T Jr, Jacobi P A. Org. Lett., 2007, 9(17): 3221. Cited in this article [1]

[96]	Onyango E O, Jacobi P A. J. Org. Chem., 2012, 77(17): 7411. Cited in this article [1]

[97]	Smith M W, Zhou Z Y, Gao A X, Shimbayashi T, Snyder S A. Org. Lett., 2017, 19(5): 1004. Cited in this article [1]

Funding

China Petroleum and Chemical Corporation funded project(P23232)

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Received	Revised	Published
2024-03-30	2024-08-19	2024-12-24
Issue Date
2024-09-06

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