Research Process on Photoinduced Copper-Catalyzed Decarboxylative Coupling Reactions of Carboxylic Acids and Their Derivatives

Yanhong Liu; Dongju Zhang

doi:10.7536/PC240411

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Prog Chem ›› 2025, Vol. 37 ›› Issue (2) : 281-292. DOI: 10.7536/PC240411

Review

Research Process on Photoinduced Copper-Catalyzed Decarboxylative Coupling Reactions of Carboxylic Acids and Their Derivatives

Yanhong Liu ¹^,² ,
Dongju Zhang ³^,^*

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Abstract

The visible-light-driven copper-catalyzed decarboxylative coupling reaction of carboxylic acids and their derivatives is a novel, efficient, and green synthetic method. It allows the construction of various carbon-carbon and carbon-heteroatom bonds for the synthesis of a wide range of high-value-added chemicals, making it a hot topic in the field of modern synthetic chemistry. In recent years, researchers worldwide have conducted extensive studies in this area, achieving a series of innovative results that have been widely applied in organic synthesis, materials science, and medicinal chemistry. This paper reviews the latest experimental and theoretical advances in the visible-light-driven copper-catalyzed decarboxylative coupling reactions of carboxylic acids and their derivatives, with a focus on several typical cross-coupling reactions that form C—X (X = C, N, O, S) bonds. It also discusses the future development prospects of this catalytic method.

Contents

1 Introduction

2 Mechanism of photocatalyst and copper complex co-catalysis

3 Photocatalyst and copper complex co-catalyzed carboxylic acid (ester) decarboxylative coupling reactions

3.1 C—C coupling

3.2 C—N coupling

3.3 C—O coupling

3.4 C—S coupling

4 Conclusion and outlook

Key words

photocatalysis / copper complex / carboxylic acid / decarboxylation / cross-coupling reaction

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Yanhong Liu , Dongju Zhang. Research Process on Photoinduced Copper-Catalyzed Decarboxylative Coupling Reactions of Carboxylic Acids and Their Derivatives[J]. Progress in Chemistry. 2025, 37(2): 281-292 https://doi.org/10.7536/PC240411

References

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

[1]	Cherney A H, Kadunce N T, Reisman S E. Chem. Rev., 2015, 115(17): 9587. Cited in this article [1]

[2]	Du B N, Chan C M, Au C M, Yu W Y. Acc. Chem. Res., 2022, 55(15): 2123. Cited in this article [1]

[3]	Twilton J, Le C, Zhang P, Shaw M H, Evans R W, MacMillan D W C. Nat. Rev. Chem., 2017, 1(7): 0052. Cited in this article [1]

[4]	Lu F D, Chen J, Jiang X, Chen J R, Lu L Q, Xiao W J. Chem. Soc. Rev., 2021, 50(22): 12808. Cited in this article [1]

[5]	Chan A Y, Perry I B, Bissonnette N B, Buksh B F, Edwards G A, Frye L I, Garry O L, Lavagnino M N, Li B X, Liang Y F, Mao E, Millet A, Oakley J V, Reed N L, Sakai H A, Seath C P, MacMillan D W C. Chem. Rev., 2022, 122(2): 1485. Cited in this article [1]

[6]	Lu F D, He G F, Lu L Q, Xiao W J. Green Chem., 2021, 23(15): 5379. Cited in this article [1]

[7]	Zhang Y J, Ma D L, Zhang Z P. Arab. J. Chem., 2022, 15(7): 103922. Cited in this article [1]

[8]	Engl S, Reiser O. Chem. Soc. Rev., 2022, 51(13): 5287. Cited in this article [1]

[9]	Gavelle S, Innocent M, Aubineau T, Guérinot A. Adv. Synth. Catal., 2022, 364(24): 4189. Cited in this article [2]

[10]	Beil S B, Chen T Q, Intermaggio N E, MacMillan D W C. Acc. Chem. Res., 2022, 55(23): 3481. Cited in this article [2]

[11]	Lu Y J, Dai N N, Li M H, Tian W C, Li Q, Wang Z J, Tang K Q, Wei W T. Adv. Synth. Catal., 2024, 366(19): 4000. Cited in this article [1]

[12]	Beaudelot J, Oger S, Peruško S, Phan T A, Teunens T, Moucheron C, Evano G. Chem. Rev., 2022, 122(22): 16365. Cited in this article [1]

[13]	Cheng W M, Shang R. ACS Catal., 2020, 10(16): 9170. Cited in this article [1]

[14]	Zhang Y J, Wang Q, Yan Z S, Ma D L, Zheng Y G. Beilstein J. Org. Chem., 2021, 17: 2520. Cited in this article [1]

[15]	Ramani A, Desai B, Dholakiya B Z, Naveen T. Chem. Commun., 2022, 58(57): 7850. Cited in this article [1]

[16]	Wei Y, Hu P, Zhang M, Su W P. Chem. Rev., 2017, 117(13): 8864. Cited in this article [1]

[17]	Parida S K, Mandal T, Das S, Hota S K, De Sarkar S, Murarka S. ACS Catal., 2021, 11(3): 1640. Cited in this article [1]

[18]	Varenikov A, Shapiro E, Gandelman M. Chem. Rev., 2021, 121(1): 412. Cited in this article [1]

[19]	Prier C K, Rankic D A, MacMillan D W C. Chem. Rev., 2013, 113(7): 5322. Cited in this article [1]

[20]	Tucker J W, Stephenson C R J. J. Org. Chem., 2012, 77(4): 1617. Cited in this article [1]

[21]	Shaw M H, Twilton J, MacMillan D W C. J. Org. Chem., 2016, 81(16): 6898. Cited in this article [1]

[22]	Cheung K P S, Sarkar S, Gevorgyan V. Chem. Rev., 2022, 122(2): 1543. Cited in this article [1]

[23]	Liu L, Gu Y C, Zhang C P. J. Org. Chem., 2023, 88(13): 9372. Cited in this article [1]

[24]	Beil S B, Bonnet S, Casadevall C, Detz R J, Eisenreich F, Glover S D, Kerzig C, Næsborg L, Pullen S, Storch G, Wei N, Zeymer C. JACS Au, 2024, 4(8): 2746. Cited in this article [1]

[25]	Song L L, Cai L C, Gong L, Van der Eycken E V. Chem. Soc. Rev., 2023, 52(7): 2358. Cited in this article [1]

[26]	Ullmann F, Bielecki J. Ber. Dtsch. Chem. Ges., 1901, 34(2): 2174. Cited in this article [1]

[27]	Chodkiewicz W, Cadiot P, Hebd C R. Seances Acad. Sci., 1955, 241: 1055. Cited in this article [2]

[28]	Stephens R D, Castro C E. J. Org. Chem., 1963, 28(12): 3313. Cited in this article [2]

[29]	Corey E J, Posner G H. J. Am. Chem. Soc., 1967, 89(15): 3911. Cited in this article [2]

[30]	Salih K S M, Baqi Y. Catalysts, 2020, 10(1): 4. Cited in this article [1]

[31]	Gong L. Nat. Synth., 2022, 1(12): 915. Cited in this article [1]

[32]	Dong X Y, Li Z L, Gu Q S, Liu X Y. J. Am. Chem. Soc., 2022, 144(38): 17319. Cited in this article [1]

[33]	Choi J, Fu G C. Science, 2017, 356(6334): eaaf7230. Cited in this article [1]

[34]	Xuan J, Xiao W J. Angew. Chem. Int. Ed., 2012, 51(28): 6828. Cited in this article [1]

[35]	Acetylene Chemistry: Chemistry, Biology and Material Science. Eds.: Diederich F, Stang P, Tykwinski R. Wiley-VCH, 2004. Cited in this article [1]

[36]	Lauder K, Toscani A, Scalacci N, Castagnolo D. Chem. Rev., 2017, 117(24): 14091. Cited in this article [1]

[37]	Zhang H, Zhang P X, Jiang M, Yang H J, Fu H. Org. Lett., 2017, 19(5): 1016. Cited in this article [1]

[38]	Xia H D, Li Z L, Gu Q S, Dong X Y, Fang J H, Du X Y, Wang L L, Liu X Y. Angew. Chem. Int. Ed., 2020, 59(39): 16926. Cited in this article [1]

[39]	Wang Y B, Tan B. Acc. Chem. Res., 2018, 51(2): 534. Cited in this article [1]

[40]	Wang D H, Zhu N, Chen P H, Lin Z Y, Liu G S. J. Am. Chem. Soc., 2017, 139(44): 15632. Cited in this article [1]

[41]	Liang Y J, Sun G Y, Su Z M, Guan W. Dalton Trans., 2020, 49(43): 15276. Cited in this article [1]

[42]	Wang J, Sánchez-Roselló M, Aceña J L, del Pozo C, Sorochinsky A E, Fustero S, Soloshonok V A, Liu H. Chem. Rev., 2014, 114(4): 2432. Cited in this article [1]

[43]	Yang X Y, Wu T, Phipps R J, Toste F D. Chem. Rev., 2015, 115(2): 826. Cited in this article [1]

[44]	Zhang H R, Chen D Q, Han Y P, Qiu Y F, Jin D P, Liu X Y. Chem. Commun., 2016, 52(79): 11827. Cited in this article [1]

[45]	Purser S, Moore P R, Swallow S, Gouverneur V. Chem. Soc. Rev., 2008, 37(2): 320. Cited in this article [1]

[46]	Kautzky J A, Wang T, Evans R W, MacMillan D W C. J. Am. Chem. Soc., 2018, 140(21): 6522. Cited in this article [1]

[47]	Patel M, Desai B, Sheth A, Dholakiya B Z, Naveen T. Asian J. Org. Chem., 2021, 10(12): 3201. Cited in this article [1]

[48]	Sha W X, Deng L L, Ni S Y, Mei H B, Han J L, Pan Y. ACS Catal., 2018, 8(8): 7489. Cited in this article [1]

[49]	Lu F D, Lu L Q, He G F, Bai J C, Xiao W J. J. Am. Chem. Soc., 2021, 143(11): 4168. Cited in this article [2]

[50]	Liu Y H, Feng A L, Zhu R X, Zhang D J. Chem. Sci., 2023, 14(17): 4580. Cited in this article [1]

[51]	Duan S Z, Du Y, Wang L L, Tian X, Zi Y J, Zhang H B, Walsh P J, Yang X D. Angew. Chem. Int. Ed., 2023, 62(19): e202300605. Cited in this article [1]

[52]	Shi J, Xu Q L, Ni Y Q, Li L, Pan F. Org. Lett., 2022, 24(25): 4609. Cited in this article [1]

[53]	Treacy S M, Rovis T. J. Am. Chem. Soc., 2021, 143(7): 2729. Cited in this article [1]

[54]	Dang H T, Haug G C, Nguyen V T, Vuong N T H, Nguyen V D, Arman H D, Larionov O V. ACS Catal., 2020, 10(19): 11448. Cited in this article [1]

[55]	Hu R R, Leung N L C, Tang B Z. Chem. Soc. Rev., 2014, 43(13): 4494. Cited in this article [1]

[56]	Mu Y C, Nguyen T T, Koh M J, Schrock R R, Hoveyda A H. Nat. Chem., 2019, 11(5): 478. Cited in this article [1]

[57]	Tang F, Feng Y S, Cheng Z F, Zhang Q, Xu H J. Org. Lett., 2023, 25(21): 3916. Cited in this article [1]

[58]	Mastandrea M M, Cañellas S, Caldentey X, Pericàs M A. ACS Catal., 2020, 10(11): 6402. Cited in this article [1]

[59]	Vitaku E, Smith D T, Njardarson J T. J. Med. Chem., 2014, 57(24): 10257. Cited in this article [1]

[60]	Talekar S S, Dutta S, Mane M V, Maity B. Eur. J. Org. Chem., 2024, 27(11): e202301312. Cited in this article [1]

[61]	Monnier F, Taillefer M. Angew. Chem. Int. Ed., 2009, 48(38): 6954. Cited in this article [1]

[62]	Forero-Cortés P A, Haydl A M. Org. Process Res. Dev., 2019, 23(8): 1478. Cited in this article [1]

[63]	Ruiz-Castillo P, Buchwald S L. Chem. Rev., 2016, 116(19): 12564. Cited in this article [1]

[64]	Zhao X, Liu Y H, Zhu R X, Liu C B, Zhang D J. Inorg. Chem., 2019, 58(19): 12669. Cited in this article [2]

[65]	Till N A, Tian L, Dong Z, Scholes G D, MacMillan D W C. J. Am. Chem. Soc., 2020, 142(37): 15830. Cited in this article [1]

[66]	Bellotti P, Huang H M, Faber T, Glorius F. Chem. Rev., 2023, 123(8): 4237. Cited in this article [1]

[67]	Liang Y F, Zhang X H, MacMillan D W C. Nature, 2018, 559(7712): 83. Cited in this article [1]

[68]	Zhang X H, Smith R T, Le C, McCarver S J, Shireman B T, Carruthers N I, MacMillan D W C. Nature, 2020, 580(7802): 220. Cited in this article [1]

[69]	Mane M V, Dutta S, Cavallo L, Maity B. ACS Catal., 2023, 13(9): 6249. Cited in this article [1]

[70]	Nguyen V T, Nguyen V D, Haug G C, Vuong N T H, Dang H T, Arman H D, Larionov O V. Angew. Chem. Int. Ed., 2020, 59(20): 7921. Cited in this article [1]

[71]	Xiong N, Li Y, Zeng R. ACS Catal., 2023, 13(3): 1678. Cited in this article [1]

[72]	Mao R Z, Frey A, Balon J, Hu X L. Nat. Catal., 2018, 1(2): 120. Cited in this article [1]

[73]	Liu Y H, Yang Y Y, Zhu R X, Zhang D J. ACS Catal., 2020, 10(9): 5030. Cited in this article [1]

[74]	Mao R Z, Balon J, Hu X L. Angew. Chem. Int. Ed., 2018, 57(30): 9501. Cited in this article [1]

[75]	Barzanò G, Mao R Z, Garreau M, Waser J, Hu X L. Org. Lett., 2020, 22(14): 5412. Cited in this article [1]

[76]	DiRocco D A, Dykstra K, Krska S, Vachal P, Conway D V, Tudge M. Angew. Chem. Int. Ed., 2014, 53(19): 4802. Cited in this article [1]

[77]	Tang Z L, Ouyang X H, Song R J, Li J H. Org. Lett., 2021, 23(3): 1000. Cited in this article [1]

[78]	Nakata T. Chem. Rev., 2005, 105(12): 4314. Cited in this article [1]

[79]	Fuhrmann E, Talbiersky J. Org. Process Res. Dev., 2005, 9(2): 206. Cited in this article [1]

[80]	Caron S. Practical Synthetic Organic Chemistry. Hoboken: Wiley, 2011. 237. Cited in this article [1]

[81]	Enthaler S, Company A. Chem. Soc. Rev., 2011, 40(10): 4912. Cited in this article [1]

[82]	MacQueen P M, Tassone J P, Diaz C, Stradiotto M. J. Am. Chem. Soc., 2018, 140(15): 5023. Cited in this article [1]

[83]	Mao R Z, Balon J, Hu X L. Angew. Chem. Int. Ed., 2018, 57(41): 13624. Cited in this article [1]

[84]	Li R H, Zhao Y L, Shang Q K, Geng Y, Wang X L, Su Z M, Li G F, Guan W. ACS Catal., 2021, 11(11): 6633. Cited in this article [3]

[85]	Ma B, Chen Z Y, Ma M, Zhao Z, Long Y E, Chen D P, Yang J Y. Org. Chem. Front., 2024, 11(20): 5876. Cited in this article [1]

[86]	Chen G L, He S H, Cheng L, Liu F. Org. Lett., 2021, 23(21): 8338. Cited in this article [1]

[87]	Meek J S, Fowler J S. J. Org. Chem., 1968, 33(9): 3422. Cited in this article [1]

[88]	Gilman H, Fothergill R E. J. Am. Chem. Soc., 1929, 51(11): 3501. Cited in this article [1]

[89]	Qiu G, Zhou K D, Gao L, Wu J. Org. Chem. Front., 2018, 5(4): 691. Cited in this article [1]

[90]	Mulina O M, Ilovaisky A I, Parshin V D, Terent’ev A O. Adv. Synth. Catal., 2020, 362(21): 4579. Cited in this article [1]

[91]	Zhou Y, Yang W H, Dai N N, Feng J Y, Yang M Q, Gao W Q, Li Q, Deng C, Lu Z, Wei W T. Org. Lett., 2024, 26(24): 5074. Cited in this article [1]

[92]	Hell S M, Meyer C F, Misale A, Sap J B I, Christensen K E, Willis M C, Trabanco A A, Gouverneur V. Angew. Chem. Int. Ed., 2020, 59(28): 11620. Cited in this article [1]

[93]	Nguyen V T, Haug G C, Nguyen V D, Vuong N T H, Arman H D, Larionov O V. Chem. Sci., 2021, 12(18): 6429. Cited in this article [1]

[94]	Bentley R. Chem. Soc. Rev., 2005, 34(7): 609. Cited in this article [1]

[95]	He S H, Chen G L, Gong X Y, Ao G Z, Liu F. J. Org. Chem., 2023, 88(11): 6671. Cited in this article [1]

[96]	Yoshida S, Yano T, Misawa Y, Sugimura Y, Igawa K, Shimizu S, Tomooka K, Hosoya T. J. Am. Chem. Soc., 2015, 137(44): 14071. Cited in this article [1]

[97]	Zhang M J, Liu L X, Tan Y H, Jing Y, Liu Y X, Wang Z W, Wang Q M. Angew. Chem. Int. Ed., 2024, 63(6): e202318344. Cited in this article [1]