Recent Advances in Visible-Light-Promoted Copper Catalysis in Organic Reactions

Yang Xiong; Sijia Li; Haijing Xiao; Guozhu Zhang

doi:10.1055/a-1533-3597

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(23): 4327-4340
DOI: 10.1055/a-1533-3597

short review

Recent Advances in Visible-Light-Promoted Copper Catalysis in Organic Reactions

Yang Xiong

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China

,

Sijia Li

^aCollege of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei 430079, P. R. of China

,

Haijing Xiao

^aCollege of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei 430079, P. R. of China

,

Guozhu Zhang ∗

^aCollege of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei 430079, P. R. of China

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

In recent years, visible-light-mediated copper photocatalysis has emerged as an attractive strategy for the diverse construction of basic bonds in an ecologically benign and cost-effective fashion. The intense activity in these areas has been stimulated by the distinctive properties of copper photocatalysts and has led to the rapid development and expansion of their applications. In this review, we focus on a series of significant achievements in the use of copper complexes as standalone photocatalysts in organic reactions to exhibit their high flexibility and potential in synthetic chemistry.

1 Introduction

2 Redox Coupling Reactions

2.1 Carbon–Nitrogen Redox Coupling Reactions

2.2 Carbon–Carbon Redox Coupling Reactions

3 Oxidative Coupling Reactions

4 Difunctionalization of Olefins

5 C–H Bond Functionalization

6 Radical Alkylation of Imines

7 Conclusions and Outlook

Key words

visible-light-mediated - copper photocatalysis - cross-coupling - asymmetric - functionalization

Volltext

Referenzen

References
1 Current address: Technical University of Munich, Lichtenbergstraße 4, 85747, Garching, Germany
2 Zimmerman HE. Pure Appl. Chem. 2006; 78: 2193

3a König B. Eur. J. Org. Chem. 2017; 1979
3b Marzo L, Pagire SK, Reiser O, König B. Angew. Chem. Int. Ed. 2018; 57: 10034
3c Zho Q, Zou Y, Lu L, Xiao W. Angew. Chem. Int. Ed. 2019; 58: 1586

4a Xuan J, Xiao W. Angew. Chem. Int. Ed. 2012; 51: 6828
4b Reckenthäler M, Griesbeck AG. Adv. Synth. Catal. 2013; 355: 2727
4c Schultz DM, Yoon TP. Science 2014; 343: 1239176
4d Liu Q, Wu L. Natl. Sci. Rev. 2017; 4: 359

5a Narayanam JM. R, Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102
5b Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
5c Hari DP, König B. Angew. Chem. Int. Ed. 2013; 52: 4734
5d Brimioulle R, Lenhart D, Maturi MM, Bach T. Angew. Chem. Int. Ed. 2015; 54: 3872
5e Shaw MH, Twilton J, MacMillan DW. C. J. Org. Chem. 2016; 81: 6898
5f Kärkäs MD, Porco JA. Jr, Stephenson CR. J. Chem. Rev. 2016; 116: 9683
5g Ravelli D, Protti S, Fagnoni M. Chem. Rev. 2016; 116: 9850
5h Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075

6a Paria S, Reiser O. ChemCatChem 2014; 6: 2477
6b Fumagalli G, Rabet PT. G, Boyd S, Greaney MF. Angew. Chem. Int. Ed. 2015; 54: 11481
6c Parasram M, Gevorgyan V. Chem. Soc. Rev. 2017; 46: 6227

7a Reiser O. Acc. Chem. Res. 2016; 49: 1990
7b Larsen CB, Wenger OS. Chem. Eur. J. 2018; 24: 2039
7c Hernandez-Perez AC, Collins SK. Acc. Chem. Res. 2016; 49: 1557

8a Hossain A, Bhattacharyya A, Reiser O. Science 2019; 364: eaav9713
8b Cheng W, Shang R. ACS Catal. 2020; 10: 9170

9a Roughley SD, Jordan AM. J. Med. Chem. 2011; 54: 3451
9b Fischer C, Koenig B. Beilstein J. Org. Chem. 2011; 7: 59
9c Caruano J, Muccioli GG, Robiette R. Org. Biomol. Chem. 2016; 14: 10134
9d Liang Y, Zhang X, MacMillan DW. C. Nature 2018; 559: 83

10 Bhunia S, Pawar GG, Kumar SV, Jiang Y, Ma D. Angew. Chem. Int. Ed. 2017; 56: 16136
11 Creutz SE, Lotito KJ, Fu GC, Peters JC. Science 2012; 338: 647

12a Uyeda C, Tan Y, Fu GC, Peters JC. J. Am. Chem. Soc. 2013; 135: 9548
12b Bissember AC, Lundgren RJ, Creutz SE, Peters JC, Fu GC. Angew. Chem. Int. Ed. 2013; 52: 5129
12c Ziegler DT, Choi J, Muñoz-Molina JM, Bissember AC, Peters JC, Fu GC. J. Am. Chem. Soc. 2013; 135: 13107
12d Do HQ, Bachman S, Bissember AC, Peters JC, Fu GC. J. Am. Chem. Soc. 2014; 136: 2162
12e Tan Y, Muñoz-Molina JM, Fu GC, Peters JC. Chem. Sci. 2014; 5: 2831
12f Ratani TS, Bachman S, Fu GC, Peters JC. J. Am. Chem. Soc. 2015; 137: 13902
12g Ahn JM, Peters JC, Fu GC. J. Am. Chem. Soc. 2017; 139: 18101

13 Kainz QM, Matier CD, Bartoszewicz A, Zultanski SL, Peters JC, Fu GC. Science 2016; 351: 681
14 Ahn JM, Peters JC, Fu GC. J. Am. Chem. Soc. 2017; 139: 18101
15 Zhao W, Wurz RP, Peters JP, Fu GC. J. Am. Chem. Soc. 2017; 139: 12153
16 Matier CD, Schwaben J, Peters JC, Fu GC. J. Am. Chem. Soc. 2017; 139: 17707
17 Lu B, Cheng Y, Chen LY, Chen JR, Xiao W. ACS Catal. 2019; 9: 8159
18 Dong X, Zhang Y, Ma C, Gu Q, Wang F, Li Z, Jiang S, Liu X. Nat. Chem. 2019; 11: 1158
19 Hazra A, Lee MT, Chiu JF, Lalic G. Angew. Chem. Int. Ed. 2018; 57: 5492
20 Mao Y, Zhao WX, Lu S, Yu L, Wang Y, Liang Y, Ni SY, Pan Y. Chem. Sci. 2020; 11: 4939
21 Xia H, Li Z, Gu Q, Dong X, Fang J, Du X, Wang L, Liu X. Angew. Chem. Int. Ed. 2020; 59: 16926
22 Liang L, Niu H, Li R, Wang Y, Yan J, Li C, Hai M. Org. Lett. 2020; 22: 6842
23 Minozzi C, Caron A, Grenier-Petel JC, Santandrea J, Collins SK. Angew. Chem. Int. Ed. 2018; 57: 5477
24 Caron A, Morin É, Collins SK. ACS Catal. 2019; 9: 9458

25a Sagadevan A, Hwang KC. Adv. Synth. Catal. 2012; 354: 3421
25b Sagadevan A, Ragupathi A, Hwang KC. Angew. Chem. Int. Ed. 2015; 54: 13896
25c Sagadevan A, Ragupathi A, Lin C, Hwu JR, Hwang KC. Green Chem. 2015; 17: 1113
25d Sagadevan A, Charpe VP, Hwang KC. Catal. Sci. Technol. 2016; 6: 7688

26 Sagadevan A, Lyu PC, Hwang KC. Green Chem. 2016; 18: 4526
27 Sagadevan A, Charpe VP, Ragupathi A, Hwang KC. J. Am. Chem. Soc. 2017; 139: 2896
28 Das DK, Pampana VK, Hwang KC. Chem. Sci. 2018; 9: 7318
29 Sagadevan A, Pampana VK, Hwang KC. Angew. Chem. Int. Ed. 2019; 58: 3838
30 Charpe VP, Sagadevan A, Hwang KC. Green Chem. 2020; 22: 4426
31 Lan X, Wang N, Xing Y. Eur. J. Org. Chem. 2017; 5821

32a Pirtsch M, Paria S, Matsuno T, Isobe H, Reiser O. Chem. Eur. J. 2012; 18: 7336
32b Paria S, Pirtsch M, Kais V, Reiser O. Synthesis 2013; 45: 2689
32c Bagal DB, Kachkovskyi G, Knorn M, Rawner T, Bhanage BM, Reiser O. Angew. Chem. Int. Ed. 2015; 54: 6999
32d Knorn M, Rawner T, Czerwieniec R, Reiser O. ACS Catal. 2015; 5: 5186

33 Abderrazak Y, Bhattacharyya A, Reiser O. Angew. Chem. Int. Ed. 2021; in press
34 Hossain A, Vidyasagar A, Eichinger C, Lankes C, Phan J, Rehbein J, Reiser O. Angew. Chem. Int. Ed. 2018; 57: 8288
35 Rawner T, Lutsker E, Kaiser CA, Reiser O. ACS Catal. 2018; 8: 3950
36 Hossain A, Engl S, Lutsker E, Reiser O. ACS Catal. 2019; 9: 1103
37 Engl S, Reiser O. ACS Catal. 2020; 10: 9899

38a Fayad R, Engl S, Danilov EO, Hauke CE, Reiser O, Castellano FN. J. Phys. Chem. Lett. 2020; 11: 5345
38b Engl S, Reiser O. Eur. J. Org. Chem. 2020; 1523

39 Kochi JK. J. Am. Chem. Soc. 1962; 84: 2121
40 Lian P, Long W, Li J, Zheng Y, Wan X. Angew. Chem. Int. Ed. 2020; 59: 23603
41 Treacy SM, Rovis T. J. Am. Chem. Soc. 2021; 143: 2729
42 Liu Z, Chen H, Lv Y, Tan X, Shen H, Yu H, Li C. J. Am. Chem. Soc. 2018; 140: 6169
43 He J, Chen C, Fu GC, Peters JC. ACS Catal. 2018; 8: 11741

44a Xiong Y, Zhang G. J. Am. Chem. Soc. 2018; 140: 2735
44b Xiong Y, Su Y, Zhang G. Org. Lett. 2018; 20: 6250

45a Xiong Y, Ma X, Zhang G. Org. Lett. 2019; 21: 1699
45b Xiong Y, Zhang G. Org. Lett. 2019; 21: 7873

46a Zhang Y, Sun Y, Chen B, Xu M, Li C, Zhang D, Zhang G. Org. Lett. 2020; 22: 1490
46b Guo Q, Wang M, Peng Q, Huo Y, Liu Q, Wang R, Xu Z. ACS Catal. 2019; 9: 4470

47 Yu X, Zhao Q, Chen J, Chen J, Xiao W. Angew. Chem. Int. Ed. 2018; 57: 15731
48 Chen J, He B, Wang P, Yu X, Zhao Q, Chen J, Xiao W. Org. Lett. 2019; 21: 4359
49 Lou J, Ma J, Xu BH, Zhou Y, Yu Z. Org. Lett. 2020; 22: 5202
50 Lei W, Wang T, Feng K, Wu L, Liu Q. ACS Catal. 2017; 7: 7941

51a Davies HM. L. Angew. Chem. Int. Ed. 2006; 45: 6422
51b Davies HM. L, Du BJ, Yu J. Chem. Soc. Rev. 2011; 40: 1855

52 Rabet PT. G, Fumagalli G, Boyd S, Greaney MF. Org. Lett. 2016; 18: 1646
53 Nicholls TP, Constable GE, Robertson JC, Gardiner MG, Bissember AC. ACS Catal. 2016; 6: 451
54 Meng Q, Gao X, Lei T, Liu Z, Zhan F, Li Z, Zhong J, Xiao H, Feng K, Chen B, Tao Y, Tung C, Wu L. Sci. Adv. 2017; 3: e1700666
55 Song Z, Liu Z, Gan Q, Lei T, Tung C, Wu L. Org. Lett. 2020; 22: 832
56 Michelet B, Deldaele C, Kajouj S, Moucheron C, Evano G. Org. Lett. 2017; 19: 3576
57 Wang C, Guo M, Qi R, Shang Q, Liu Q, Wang S, Zhao L, Wang R, Xu Z. Angew. Chem. Int. Ed. 2018; 57: 15841
58 Lyu X, Huang S, Song H, Liu Y, Wang Q. Org. Lett. 2019; 21: 5728
59 Wang C, Yu Y, Liu W, Duan W. Org. Lett. 2019; 21: 9147
60 Zheng L, Jiang Q, Bao H, Zhou B, Luo S, Jin H, Wu H, Liu Y. Org. Lett. 2020; 22: 8888

61a Li C, Chen B, Ma X, Mo X, Zhang G. Angew. Chem. Int. Ed. 2021; 60: 2130
61b Ma X, Zhang G. Chin. J. Chem. 2020; 38: 1299

62 Cao Z, Li J, Sun Y, Zhang H, Mo X, Cao X, Zhang G. Chem. Sci. 2021; 12: 4836
63 Li Y, Zhou K, Wen Z, Cao S, Shen X, Lei M, Gong L. J. Am. Chem. Soc. 2018; 140: 15850
64 Han B, Li YJ, Yu Y, Gong L. Nat. Commun. 2019; 10: 3804