Recent Advances in Photocatalytic C–N Bond Coupling Reactions

Chun-Ming Chan; Yip-Chi Chow; Wing-Yiu Yu

doi:10.1055/s-0040-1707136

Synthesis, Table of Contents

Synthesis 2020; 52(20): 2899-2921
DOI: 10.1055/s-0040-1707136

review

Recent Advances in Photocatalytic C–N Bond Coupling Reactions

Authors

Chun-Ming Chan
Yip-Chi Chow
Wing-Yiu Yu ∗

State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong Email: wing-yiu.yu@polyu.edu.hk

Abstract

All articles of this category

Abstract

Catalytic C–N bond formation is one of the major research topics in synthetic chemistry owing to the ubiquity of amino groups in natural products, synthetic intermediates and pharmaceutical agents. In parallel with well-established metal-catalyzed C–N bond coupling protocols, photocatalytic reactions have recently emerged as efficient and selective alternatives for the construction of C–N bonds. In this review, the progress made on photocatalytic C–N bond coupling reactions between 2012 and February 2020 is summarized.

1 Introduction

1.1 General Mechanisms for Photoredox Catalysis

1.2 Pioneering Work

2 C(sp²)–N Bond Formation

2.1 Protocols Involving an External Oxidant

2.2 Oxidant-Free Protocols

3 C(sp³)–N Bond Formation

3.1 Direct Radical–Radical Coupling

3.2 Addition Reactions to Alkenes

3.3 Reductive Amination of Carbonyl Compounds

3.4 Decarboxylative Amination

4 Cyclization Reactions

4.1 C(sp²)–N Heterocycle Formation

4.2 C(sp³)–N Heterocycle Formation

5 Other Examples

6 Conclusion and Outlook

Key words

photochemistry - C–N cross-coupling - amination - radicals - visible light

Full Text

References

References

1a Nugent TC. Chiral Amine Synthesis: Methods, Developments and Applications. Wiley-VCH; Weinheim: 2010
1b Quintás-Cardama A, Kantarjian H, Cortes J. Nat. Rev. Drug Discovery 2007; 6: 834
1c Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893

2a Trowbridge A, Walton SM, Gaunt MJ. Chem. Rev. 2020; 120: 2613
2b Xiong P, Xu H.-C. Acc. Chem. Res. 2019; 52: 3339
2c Park Y, Kim Y, Chang S. Chem. Rev. 2017; 117: 9247
2d Bariwal J, Van der Eycken EV. Chem. Soc. Rev. 2013; 42: 9283
2e Beletskaya IP, Cheprakov AV. Organometallics 2012; 31: 7753

3a Bhunia S, Pawar GG, Kumar SV, Jiang Y, Ma D. Angew. Chem. Int. Ed. 2017; 56: 16136
3b Sambiagio C, Marsden SP, Blacker AJ, McGowan PC. Chem. Soc. Rev. 2014; 43: 3525

For a review on the Buchwald–Hartwig coupling, see:

4a Heravi MM, Kheilkordi Z, Zadsirjan V, Heydari M, Malmir M. J. Organomet. Chem. 2018; 861: 17
4b For a review on the Chan–Evans–Lam coupling, see: West MJ, Fyfe JW. B, Vantourout JC, Watson AJ. B. Chem. Rev. 2019; 119: 12491

5a Gandeepan P, Müller T, Zell D, Cera G, Warratz S, Ackermann L. Chem. Rev. 2019; 119: 2192
5b Stateman LM, Nakafuku KM, Nagib DA. Synthesis 2018; 50: 1569
5c Zhang H, Lei A. Asian J. Org. Chem. 2018; 7: 1164
5d Zhang H, Lei A. Synthesis 2018; 51: 83

6a Liu W, Li J, Querard P, Li C.-J. J. Am. Chem. Soc. 2019; 141: 6755
6b Festa AA, Voskressensky LG, Van der Eycken EV. Chem. Soc. Rev. 2019; 48: 4401
6c Uygur M, Garcia Mancheño O. Org. Biomol. Chem. 2019; 17: 5475
6d An X.-D, Yu S. Tetrahedron Lett. 2018; 59: 1605
6e Yan M, Lo JC, Edwards JT, Baran PS. J. Am. Chem. Soc. 2016; 138: 12692
6f Staveness D, Bosque I, Stephenson CR. J. Acc. Chem. Res. 2016; 49: 2295
6g Chen J.-R, Hu X.-Q, Lu L.-Q, Xiao W.-J. Chem. Soc. Rev. 2016; 45: 2044
6h Narayanam JM. R, Stephenson CR. Chem. Soc. Rev. 2011; 40: 102
6i Zeitler K. Angew. Chem. Int. Ed. 2009; 48: 9785

7 Yoon TP, Ischay MA, Du J. Nat. Chem. 2010; 2: 527

For reviews on C–N coupling using Ru/Ir-based polypyridyl complexes, see:

8a Angerani S, Winssinger N. Chem. Eur. J. 2019; 25: 6661
8b Huang X, Meggers E. Acc. Chem. Res. 2019; 52: 833
8c Lekkala R, Lekkala R, Moku B, Rakesh KP, Qin H.-L. Eur. J. Org. Chem. 2019; 2769
8d Xia Q, Dong J, Song H, Wang Q. Chem. Eur. J. 2019; 25: 2949
8e Wang C.-S, Dixneuf PH, Soulé J.-F. Chem. Rev. 2018; 118: 7532
8f Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
8g Xi Y, Yi H, Lei A. Org. Biomol. Chem. 2013; 11: 2387

For reviews on C–N coupling using organic dyes, see:

8h Sharma S, Sharma A. Org. Biomol. Chem. 2019; 17: 4384
8i Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
8j Fukuzumi S, Ohkubo K. Org. Biomol. Chem. 2014; 12: 6059
8k Rochkind M, Pasternak S, Paz Y. Molecules 2014; 20: 88
8l Nicewicz DA, Nguyen TM. ACS Catal. 2013; 4: 355
8m Ravelli D, Fagnoni M, Albini A. Chem. Soc. Rev. 2013; 42: 97

9a Luo J, Wei W.-T. Adv. Synth. Catal. 2018; 360: 2076
9b Zhao Y, Xia W. Chem. Soc. Rev. 2018; 47: 2591
9c Kärkäs MD. ACS Catal. 2017; 7: 4999
9d Menigaux D, Belmont P, Brachet E. Eur. J. Org. Chem. 2017; 2008
9e Taniguchi T. Synthesis 2017; 49: 3511
9f Xiong T, Zhang Q. Chem. Soc. Rev. 2016; 45: 3069

10 Creutz SE, Lotito KJ, Fu GC, Peters JC. Science 2012; 338: 647
11 Maity S, Zheng N. Angew. Chem. Int. Ed. 2012; 51: 9562
12 Cecere G, König CM, Alleva JL, MacMillan DW. C. J. Am. Chem. Soc. 2013; 135: 11521
13 Allen LJ, Cabrera PJ, Lee M, Sanford MS. J. Am. Chem. Soc. 2014; 136: 5607
14 Liu J, Liu Q, Yi H, Qin C, Bai R, Qi X, Lan Y, Lei A. Angew. Chem. Int. Ed. 2014; 53: 502

15a Romero NA, Margrey KA, Tay NE, Nicewicz DA. Science 2015; 349: 1326
15b Margrey KA, Levens A, Nicewicz DA. Angew. Chem. Int. Ed. 2017; 56: 15644
15c Margrey KA, McManus JB, Bonazzi S, Zecri F, Nicewicz DA. J. Am. Chem. Soc. 2017; 139: 11288

16a Meyer AU, Berger AL, König B. Chem. Commun. 2016; 52: 10918
16b Das S, Natarajan P, König B. Chem. Eur. J. 2017; 23: 18161
16c Song C, Yi H, Dou B, Li Y, Singh AK, Lei A. Chem. Commun. 2017; 53: 3689

17 Pandey G, Singh D, Laha R. Asian J. Org. Chem. 2017; 6: 469

18a Samanta S, Ravi C, Rao SN, Joshi A, Adimurthy S. Org. Biomol. Chem. 2017; 15: 9590
18b You G, Wang K, Wang X, Wang G, Sun J, Duan G, Xia C. Org. Lett. 2018; 20: 4005

19 Zhang L, Liardet L, Luo J, Ren D, Grätzel M, Hu X. Nat. Catal. 2019; 2: 366
20 Tong K, Liu X, Zhang Y, Yu S. Chem. Eur. J. 2016; 22: 15669

21a Ito E, Fukushima T, Kawakami T, Murakami K, Itami K. Chem 2017; 2: 383
21b Yamaguchi T, Yamaguchi E, Itoh A. Org. Lett. 2017; 19: 1282

22 Zhao Y, Huang B, Yang C, Li B, Gou B, Xia W. ACS Catal. 2017; 7: 2446
23 Xin J.-R, He Y.-H, Guan Z. Org. Chem. Front. 2018; 5: 1684
24 Ruffoni A, Juliá F, Svejstrup TD, McMillan AJ, Douglas JJ, Leonori D. Nat. Chem. 2019; 11: 426
25 Leow D. Org. Lett. 2014; 16: 5812

26a Leung FK.-C, Cui J.-F, Hui T.-W, Kung KK.-Y, Wong M.-K. Asian J. Org. Chem. 2015; 4: 533
26b Monga A, Pandey AP, Sharma A. Adv. Synth. Catal. 2019; 361: 3554

27 Song W, Dong K, Li M. Org. Lett. 2020; 22: 371
28 Kaur S, Kumar M, Bhalla V. Green Chem. 2016; 18: 5870
29 Kudisch M, Lim C.-H, Thordarson P, Miyake GM. J. Am. Chem. Soc. 2019; 141: 19479
30 Kim H, Kim T, Lee DG, Roh SW, Lee C. Chem. Commun. 2014; 50: 9273

31a Qin Q, Yu S. Org. Lett. 2014; 16: 3504
31b Zhang M, Duan Y, Li W, Xu P, Cheng J, Yu S, Zhu C. Org. Lett. 2016; 18: 5356

32 Greulich TW, Daniliuc CG, Studer A. Org. Lett. 2015; 17: 254
33 Brachet E, Ghosh T, Ghosh I, König B. Chem. Sci. 2015; 6: 987
34 Hillenbrand J, Ham WS, Ritter T. Org. Lett. 2019; 21: 5363
35 Zheng Y.-W, Chen B, Ye P, Feng K, Wang W, Meng Q.-Y, Wu L.-Z, Tung C.-H. J. Am. Chem. Soc. 2016; 138: 10080

36a Niu L, Yi H, Wang S, Liu T, Liu J, Lei A. Nat. Commun. 2017; 8: 14226
36b Chen H, Yi H, Tang Z, Bian C, Zhang H, Lei A. Adv. Synth. Catal. 2018; 360: 3220
36c Yi H, Niu L, Song C, Li Y, Dou B, Singh AK, Lei A. Angew. Chem. Int. Ed. 2017; 56: 1120

37 Zhao F, Yang Q, Zhang J, Shi W, Hu H, Liang F, Wei W, Zhou S. Org. Lett. 2018; 20: 7753

38a Yoo W.-J, Tsukamoto T, Kobayashi S. Org. Lett. 2015; 17: 3640
38b Yoo W.-J, Tsukamoto T, Kobayashi S. Angew. Chem. Int. Ed. 2015; 54: 6587

39 Engl PS, Häring AP, Berger F, Berger G, Pérez-Bitrián A, Ritter T. J. Am. Chem. Soc. 2019; 141: 13346
40 Kainz QM, Matier CD, Bartoszewicz A, Zultanski SL, Peters JC, Fu GC. Science 2016; 351: 681
41 Zhang L, Yi H, Wang J, Lei A. J. Org. Chem. 2017; 82: 10704
42 Zhao W, Wurz RP, Peters JC, Fu GC. J. Am. Chem. Soc. 2017; 139: 12153
43 Bosnidou AE, Muñiz K. Angew. Chem. Int. Ed. 2019; 58: 7485
44 Chan C.-M, Xing Q, Chow Y.-C, Hung S.-F, Yu W.-Y. Org. Lett. 2019; 21: 8037
45 Soni VK, Lee S, Kang J, Moon YK, Hwang HS, You Y, Cho EJ. ACS Catal. 2019; 9: 10454
46 Angnes RA, Potnis C, Liang S, Correia CR. D, Hammond GB. J. Org. Chem. 2020; 85: 4153
47 Miyazawa K, Koike T, Akita M. Chem. Eur. J. 2015; 21: 11677
48 Qin Q, Ren D, Yu S. Org. Biomol. Chem. 2015; 13: 10295

49a Musacchio AJ, Lainhart BC, Zhang X, Naguib SG, Sherwood TC, Knowles RR. Science 2017; 355: 727
49b Miller DC, Ganley JM, Musacchio AJ, Sherwood TC, Ewing WR, Knowles RR. J. Am. Chem. Soc. 2019; 141: 16590

50a Jiang H, Studer A. Angew. Chem. Int. Ed. 2018; 57: 10707
50b Jiang H, Studer A. Chem. Eur. J. 2019; 25: 516

51 Goliszewska K, Rybicka-Jasińska K, Szurmak J, Gryko D. J. Org. Chem. 2019; 84: 15834
52 Guo X, Wenger OS. Angew. Chem. Int. Ed. 2018; 57: 2469
53 Alam R, Molander GA. Org. Lett. 2018; 20: 2680

54a Lang SB, Cartwright KC, Welter RS, Locascio TM, Tunge JA. Eur. J. Org. Chem. 2016; 3331
54b Zhang M.-J, Schroeder GM, He Y.-H, Guan Z. RSC Adv. 2016; 6: 96693

55 Mao R, Frey A, Balon J, Hu X. Nat. Catal. 2018; 1: 120
56 Feng G, Wang X, Jin J. Eur. J. Org. Chem. 2019; 6728
57 Nguyen VT, Nguyen VD, Haug GC, Vuong NT. H, Dang HT, Arman HD, Larionov O. Angew. Chem. Int. Ed. 2020; 59: 7921
58 Kim JH, Ruffoni A, Al-Faiyz YS. S, Sheikh NS, Leonori D. Angew. Chem. Int. Ed. 2020; 59: 8225
59 Choi S, Chatterjee T, Choi WJ, You Y, Cho EJ. ACS Catal. 2015; 5: 4796
60 Martínez C, Bosnidou AE, Allmendinger S, Muñiz K. Chem. Eur. J. 2016; 22: 9929
61 Moon Y, Jang E, Choi S, Hong S. Org. Lett. 2018; 20: 240

62a Jiang H, An X, Tong K, Zheng T, Zhang Y, Yu S. Angew. Chem. Int. Ed. 2015; 54: 4055
62b Li G, He R, Liu Q, Wang Z, Liu Y, Wang Q. J. Org. Chem. 2019; 84: 8646

63 Wang N, Gu Q.-S, Li Z.-L, Li Z, Guo Y.-L, Guo Z, Liu X.-Y. Angew. Chem. Int. Ed. 2018; 57: 14225
64 An X.-D, Yu S. Org. Lett. 2015; 17: 2692
65 Li Z, Song H, Guo R, Zuo M, Hou C, Sun S, He X, Sun Z, Chu W. Green Chem. 2019; 21: 3602

66a Musacchio AJ, Nguyen LQ, Beard GH, Knowles RR. J. Am. Chem. Soc. 2014; 136: 12217
66b Choi GJ, Knowles RR. J. Am. Chem. Soc. 2015; 137: 9226
66c Miller DC, Choi GJ, Orbe HS, Knowles RR. J. Am. Chem. Soc. 2015; 137: 13492

67 Nguyen ST, Zhu Q, Knowles RR. ACS Catal. 2019; 9: 4502

68a Hu X.-Q, Chen J.-R, Wei Q, Liu F.-L, Deng Q.-H, Beauchemin AM, Xiao W.-J. Angew. Chem. Int. Ed. 2014; 126: 12359
68b Hu X.-Q, Qi X, Chen J.-R, Zhao Q.-Q, Wei Q, Lan Y, Xiao W.-J. Nat. Commun. 2016; 7: 11188
68c For a recent example by Chen, Xiao and co-workers, see: Zhao Q.-Q, Zhou X.-S, Xu S.-H, Wu Y.-L, Xiao W.-J, Chen J.-R. Org. Lett. 2020; 22: 2470

69a Davies J, Booth SG, Essafi S, Dryfe RA. W, Leonori D. Angew. Chem. Int. Ed. 2015; 54: 14017
69b Davies J, Svejstrup TD, Reina DF, Sheikh NS, Leonori D. J. Am. Chem. Soc. 2016; 138: 8092

70 Becker MR, Richardson AD, Schindler CS. Nat. Commun. 2019; 10: 5095
71 Zhang Y, Cao Y, Lu L, Zhang S, Bao W, Huang S, Rao Y. J. Org. Chem. 2019; 84: 7711
72 Liang D, Tan L.-P, Xiao W.-J, Chen J.-R. Chem. Commun. 2020; 56: 3777
73 Yang X, Zhu Y, Xie Z, Li Y, Zhang Y. Org. Lett. 2020; 22: 1638

74a Martínez C, Muñiz K. Angew. Chem. Int. Ed. 2015; 54: 8287
74b Becker P, Duhamel T, Stein CJ, Reiher M, Muñiz K. Angew. Chem. Int. Ed. 2017; 56: 8004
74c Becker P, Duhamel T, Martinez C, Muñiz K. Angew. Chem. Int. Ed. 2018; 57: 5166

75 Xuan J, Feng Z.-J, Duan S.-W, Xiao W.-J. RSC Adv. 2012; 2: 4065
76 Qin Q, Yu S. Org. Lett. 2015; 17: 1894

77a Davies J, Sheikh NS, Leonori D. Angew. Chem. Int. Ed. 2017; 56: 13361
77b Jiang H, Studer A. Angew. Chem. Int. Ed. 2017; 56: 12273

78 Chen J, Guo H.-M, Zhao Q.-Q, Chen J.-R, Xiao W.-J. Chem. Commun. 2018; 54: 6780
79 Zhu Q, Graff DE, Knowles RR. J. Am. Chem. Soc. 2018; 140: 741
80 Jing D, Lu C, Chen Z, Jin S, Xie L, Meng Z, Su Z, Zheng K. Angew. Chem. Int. Ed. 2019; 58: 14666

81a Gulzar N, Klussmann M. Org. Biomol. Chem. 2013; 11: 4516
81b Gulzar N, Jones KM, Konnerth H, Breugst M, Klussmann M. Chem. Eur. J. 2015; 21: 3367

82a Pandey G, Laha R. Angew. Chem. Int. Ed. 2015; 54: 14875
82b Pandey G, Laha R, Singh D. J. Org. Chem. 2016; 81: 7161

83 Sagadevan A, Ragupathi A, Lin C.-C, Hwu JR, Hwang KC. Green Chem. 2015; 17: 1113
84 Lanzi M, Merad J, Boyarskaya DV, Maestri G, Allain C, Masson G. Org. Lett. 2018; 20: 5247
85 Soni VK, Hwang HS, Moon YK, Park S.-W, You Y, Cho EJ. J. Am. Chem. Soc. 2019; 141: 10538
86 Ding R, Chen H, Xu Y.-L, Tang H.-T, Chen Y.-Y, Pan Y.-M. Adv. Synth. Catal. 2019; 361: 3656
87 Shukla G, Alam T, Srivastava HK, Kumar R, Patel BK. Org. Lett. 2019; 21: 3543