Visible-light-induced Synthesis of Organic Peroxides via Decarboxylative Couplings of Carboxylic Acids, Alkenes and tert-Butyl Hydroperoxide

Abstract

Herein, we present a photoinduced, CeCl₃-catalyzed three-component decarboxylative reaction that couples carboxylic acids, alkenes and tert-butyl hydroperoxide for the formation of various organic peroxides. The ligand-to-metal charge transfer (LMCT) excitation mode allows the decarboxylative alkylation-peroxidation reaction to occur under mild conditions, and is well applicable to primary, secondary and tertiary carboxylic acids and styrene derivatives.

Keywords

Visible-light catalysis / Difunctionalization / Carboxylic acid / Alkene / Organic peroxide

References

[1] Dömling A, Wang W, Wang K. Chem. Rev.. 2012, 112: 3083

[2] Jiang H, Studer A. Chem. Soc. Rev.. 2020, 49: 1790

[3] Li Z-L, Fang G-C, Gu Q-S, Liu X-Y. Chem. Soc. Rev.. 2020, 49: 32

[4] Staveness D, Bosque I, Stephenson C R J. Acc. Chem. Res.. 2016, 49: 2295

[5] Romero N A, Nicewicz D A. Chem. Rev.. 2016, 116: 10075

[6] Strieth-Kalthoff F, James M J, Teders M, Pitzer L. Chem. Soc. Rev.. 2018, 47: 7190

[7] Wang P-Z, Xiao W-J, Chen J-R. Nat. Rev. Chem.. 2023, 7: 35

[8] Abderrazak Y, Bhattacharyya A, Reiser O. Angew. Chem. Int. Ed.. 2021, 60: 21100

[9] Li H-C, Li G-N, Wang HS, Tan Y, Chen X-L, Yu B. Org. Chem. Front.. 2024, 11: 135

[10] Wang Y-M, Wang J-B, Huang J, Cui Z-S, Zhang M, Zhang Z-H. J. Catal.. 2023, 427: 115100

[11] Liu Q-H, Kang S-L, Cui Z-S, Liu Y-H, Zhang M, Zhang Z-H. Green Chem.. 2024, 26: 4803

[12] Huang J, Liu Y, Tian X, Ni S-F, Li S, Zhang Z-H, Li D, Liu S. Green Chem.. 2024, 26: 6559

[13] Lu Y-C, West J G. Angew. Chem. Int. Ed.. 2023, 62: e202213055

[14] Hu J, Zhu Z, Xie Z, Le Z. Chin. J. Org. Chem.. 2022, 42: 978

[15] Schwarz J, König B. Green Chem.. 2018, 20: 323

[16] Gavelle S, Innocent M, Aubineau T, Guérinot A. Adv. Synth. Catal.. 2022, 364: 4189

[17] Li L., Yao Y., Fu N., Eur. J. Org. Chem., 2023, e202300166.

[18] Huang H, Jia K, Chen Y. ACS Catal.. 2016, 6: 4983

[19] Griffin J D, Zeller M A, Nicewicz D A. J. Am. Chem. Soc.. 2015, 137: 11340

[20] Patra T, Mukherjee S, Ma J. Angew. Chem. Int. Ed.. 2019, 58: 10514

[21] Huang Z, Zhao Z, Zhang C, Lu J, Liu H, Luo N, Zhang J, Wang F. Nat. Catal.. 2020, 3: 170

[22] Sun Y-L, Tan F-F, Hu R-G, Hu C-H, Li Y. Chin. J. Chem.. 2022, 40: 1903

[23] Xu P, López-Rojas P, Ritter T. J. Am. Chem. Soc.. 2021, 143: 5349

[24] Chen T Q, Pedersen P S, Dow N W, Fayad R, Hauke C E, Rosko M C, Danilov E O, Blakemore D C, Dechert-Schmitt A-M, Knauber T, Castellano F N, MacMillan D W C. J. Am. Chem. Soc.. 2022, 144: 8296

[25] Zhang Y, Qian J, Wang M, Huang Y, Hu P. Org. Lett.. 2022, 24: 5972

[26] Xu Y, Huang P, Jiang Y, Lv C, Li P, Wang J, Sun B, Jin C. Green Chem.. 2023, 25: 8741

[27] Feng Q, Song Q. J. Org. Chem.. 2014, 79: 1867

[28] Guan R, Bennett E L, Huang Z, Xiao J. Green Chem.. 2022, 24: 2946

[29] Meng X, Xu H, Zheng Y, Luo J, Huang S. ACS Sustainable Chem. Eng.. 2022, 10: 5067

[30] Reichle A, Sterzel H, Kreitmeier P, Fayad R, Castellano F N, Rehbein J, Reiser O. Chem. Commun.. 2022, 58: 4456

[31] Candish L, Freitag M, Gensch T, Glorius F. Chem. Sci.. 2017, 8: 3618

[32] Pitchai M, Ramirez A, Mayder D M, Ulaganathan S, Kumar H, Aulakh D, Gupta A, Mathur A, Kempson J, Meanwell N, Hudson Z M, Oderinde M S. ACS Catal.. 2023, 13: 647

[33] Sun X, Ritter T. Angew. Chem. Int. Ed.. 2021, 60: 10557

[34] Moon P J, Yin S, Lundgren R J. J. Am. Chem. Soc.. 2016, 138: 13826

[35] Zhang X, Feng X, Zhou C, Yu X, Yamamoto Y, Bao M. Org. Lett.. 2018, 20: 7095

[36] Edwards J T, Merchant R R, McClymont K S, Knouse K W, Qin T, Malins L R, Vokits B, Shaw S A, Bao D-H, Wei F-L, Zhou T, Eastgate M D, Baran P S. Nature. 2017, 545: 213

[37] Lu J, Yao Y, Li L, Fu N. J. Am. Chem. Soc.. 2023, 145: 26774

[38] Mao R, Bera S, Cheseaux A, Hu X. Chem. Sci.. 2019, 10: 9555

[39] Zhang M, Xie J, Zhu C. Nat. Commun.. 2018, 9: 3518

[40] Zhang L, Chen S, He H, Li W, Zhu C, Xie J. Chem. Commun.. 2021, 57: 9064

[41] Meng L, Yang C, Dong J, Wen W, Chen J, Fan B. Org. Chem. Front.. 2024, 11: 21

[42] Wang X, Zhu B, Liu Y, Wang Q. ACS Catal.. 2022, 12: 2522

[43] Si Y-F, Chen X-L, Fu X-Y, Sun K, Song X, Qu L-B, Yu B. ACS Sustainable Chem. Eng.. 2020, 8: 10740

[44] Lu Y-H, Zhang Z-T, Wu H-Y, Zhou M-H, Song H-Y, Ji H-T, Jiang J, Chen J-Y, He W-M. Chin. Chem. Lett.. 2023, 34: 108036

[45] Lyu X-L, Huang S-S, Song H-J, Liu Y-X, Wang Q-M. Org. Lett.. 2019, 21: 5728

[46] Li H-C, Li G-N, Wang HS, Tan Y, Chen X-L, Yu B. Org. Chem. Front.. 2024, 11: 135

[47] Xu P, Su W, Ritter T. Chem. Sci.. 2022, 13: 13611

[48] Yan Z, Sun B, Huang P, Zhao H, Ding H, Su W, Jin C. Chin. Chem. Lett.. 2022, 33: 1997

[49] Si Y-F, Sun K, Chen X-L, Fu X-Y, Liu Y, Zeng F-L, Shi T, Qu L-B, Yu B. Org. Lett.. 2020, 22: 6960

[50] Zhuang K, Haug G C, Wang Y, Yin S, Sun H, Huang S, Trevino R, Shen K, Sun Y, Huang C, Qin B, Liu Y, Cheng M, Larionov O V, Jin S. J. Am. Chem. Soc.. 2024, 146: 8508

[51] Miyake Y, Nakajima K, Nishibayashi Y. Chem. Commun.. 2013, 49: 7854

[52] Chu L, Ohta C, Zuo Z, MacMillan D W C. J. Am. Chem. Soc.. 2014, 136: 10886

[53] Bao Q-F, Li M, Xia Y, Wang Y-Z, Zhou Z-Z, Liang Y-M. Org. Lett.. 2021, 23: 1107

[54] Wang A, Yin Y-Y, Rukhsana, Wang L-Q, Jin J-H, Shen Y-M. J. Org. Chem.. 2023, 88: 13871

[55] Venditto N J, Boerth J A. Org. Lett.. 2023, 25: 3429

[56] Yaremenko I A, Vil’ V A, Demchuk D V, Terent’ev A O. Beilstein J. Org. Chem.. 2016, 12: 1647

[57] Cheng J-K, Loh T-P. J. Am. Chem. Soc.. 2015, 137: 42

[58] Schweitzer-Chaput B, Demaerel J, Engler H, Klussmann M. Angew. Chem. Int. Ed.. 2014, 53: 8737

[59] Liu W, Li Y, Liu K, Li Z. J. Am. Chem. Soc.. 2011, 133: 10756

[60] Lv L, Shen B, Li Z. Angew. Chem. Int. Ed.. 2014, 53: 4164

[61] Lou C, Feng Y, Huang Q, Lv L, Li Z. Asian J. Org. Chem.. 2023, 12: e202300408

[62] Feng Y, Chen S, Lv L, Yaremenko I A, Terent’ev A O, Li Z. Org. Lett.. 2024, 26: 1920

[63] An Q, Xing Y-Y, Pu R, Jia M, Chen Y, Hu A, Zhang S-Q, Yu N, Du J, Zhang Y, Chen J, Liu W, Hong X, Zuo Z. J. Am. Chem. Soc.. 2023, 145: 359

[64] Chen Y, Wang X, He X, An Q, Zuo Z. J. Am. Chem. Soc.. 2021, 143: 4896

[65] Du J, Yang X, Wang X, An Q, He X, Pan H, Zuo Z. Angew. Chem. Int. Ed.. 2021, 60: 5370

[66] Yang Z, Yang D, Zhang J, Tan C, Li J, Wang S, Zhang H, Huang Z, Lei A. J. Am. Chem. Soc.. 2022, 144: 13895

[67] Shirase S, Tamaki S, Shinohara K, Hirosawa K, Tsurugi H, Satoh T, Mashima K. J. Am. Chem. Soc.. 2020, 142: 5668

[68] Lai X-L, Chen M, Wang Y, Song J, Xu H-C. J. Am. Chem. Soc.. 2022, 144: 20201

[69] Wang Y, Li L, Fu N. ACS Catal.. 2022, 12: 10661

[70] Li H-C, Li G-N, Sun K, Chen X-L, Jiang M-X, Qu L-B, Yu B. Org. Lett.. 2022, 24: 2431

[71] Dagar N, Singh S, Roy S R. J. Org. Chem.. 2022, 87: 8970

[72] Singh S, Dagar N, Roy S R. Chem. Commun.. 2022, 58: 3831

[73] Yatham V R, Bellotti P, König B. Chem. Commun.. 2019, 55: 3489

[74] Paquette L A. In Encyclopedia of Reagents for Organic Synthesis. 1995, New York, John Wiley & Sons, Inc

[75] Wu C-S, Li R, Wang Q-Q, Yang L. Green Chem.. 2019, 21: 269