Nickel-Catalyzed Asymmetric Cross-Electrophile Coupling Reactions

Abstract

The merger of cross-electrophile coupling and asymmetric catalysis provides a novel approach to the preparation of optically active compounds. This method is often endowed with high step economy, mild conditions, and excellent tolerance of functional groups. Recent advances in the research field of nickel-catalyzed asymmetric cross-electrophile coupling reactions are highlighted in this concise Synpacts article.

1 Introduction

2 Asymmetric Cross-Electrophile Coupling Reactions between Organohalides

3 Asymmetric Electrophilic Ring-Opening Reactions

4 Asymmetric Electrophilic Difunctionalization of Alkenes

4.1 Two-Component Electrophilic Difunctionalization of Alkenes Involving Arylnickelation as an Enantiodetermining Step

4.2 Two-Component Electrophilic Difunctionalization of Alkenes Involving Carbamoylnickelation as an Enantiodetermining Step

4.3 Three-Component Electrophilic Difunctionalization of Alkenes

5 Asymmetric Electrophilic Functionalization of Carbonyl Compounds

6 Summary

Key words

nickel catalysis - asymmetric catalysis - reductive cross-coupling - umpolung - electrophiles

• References


For reviews on Ni-catalyzed cross-electrophile coupling, see:
• 1a Everson DA, Weix DJ. J. Org. Chem. 2014; 79: 4793
• 1b Moragas T, Correa A, Martin R. Chem. Eur. J. 2014; 20: 8242
• 1c Weix DJ. Acc. Chem. Res. 2015; 48: 1767
• 1d Gu J, Wang X, Xue W, Gong H. Org. Chem. Front. 2015; 2: 1411
• 1e Wang X, Dai Y, Gong H. Top. Curr. Chem. 2016; 374: 43
• 1f Richmond E, Moran J. Synthesis 2018; 50: 499
• 2 Hao Y, Fu GC. J. Am. Chem. Soc. 2019; 141: 15433
• 3 Gutierrez O, Tellis JC, Primer DN, Molander GA, Kozlowski MC. J. Am. Chem. Soc. 2015; 137: 4896
• 4 Cherney AH, Kadunce NT, Reisman SE. J. Am. Chem. Soc. 2013; 135: 7442
• 5 Poremba KE, Kadunce NT, Suzuki N, Cherney AH, Reisman SE. J. Am. Chem. Soc. 2017; 139: 5684 ; corrigendum: J. Am. Chem. Soc. 2018, 140, 7746
• 6 Cherney AH, Reisman SE. J. Am. Chem. Soc. 2014; 136: 14365
• 7 Kadunce NT, Reisman SE. J. Am. Chem. Soc. 2015; 137: 10480
• 8 Hofstra JL, Cherney AH, Ordner CM, Reisman SE. J. Am. Chem. Soc. 2018; 140: 139
• 9 Ackerman LK. G, Anka-Lufford LL, Naodovic M, Weix DJ. Chem. Sci. 2015; 6: 1115
• 10 Suzuki N, Hofstra JL, Poremba KE, Reisman SE. Org. Lett. 2017; 19: 2150
• 11 DeLano TJ, Reisman SE. ACS Catal. 2019; 9: 6751
• 12 Guan H, Zhang Q, Walsh PJ, Mao J. Angew. Chem. Int. Ed. 2020; 59: 5172
• 13 For a review on electrophilic ring opening of small-ring molecules, see: Wang C. Synthesis 2017; 49: 5307
• 14 Zhao Y, Weix DJ. J. Am. Chem. Soc. 2015; 137: 3237
• 15 Woods BP, Orlandi M, Huang C.-Y, Sigman MS, Doyle AG. J. Am. Chem. Soc. 2017; 139: 5688 ; corrigendum: J. Am. Chem. Soc. 2018, 140, 3237
• 16 Ding D, Dong H, Wang C. iScience 2020; 23: 101017
• 17 For a review on Ni-catalyzed electrophilic difunctionalization of alkenes, see: Ping Y, Kong W. Synthesis 2020; 52: 979
• 18 Wang K, Ding Z, Zhou Z, Kong W. J. Am. Chem. Soc. 2018; 140: 12364
• 19 Li Y, Ding Z, Lei A, Kong W. Org. Chem. Front. 2019; 6: 3305
• 20 Ma T, Chen Y, Li Y, Ping Y, Kong W. ACS Catal. 2019; 9: 9127
• 21a Jin Y, Wang C. Angew. Chem. Int. Ed. 2019; 58: 6722
• 21b Jin Y, Wang C. Chem. Sci. 2019; 10: 1780
• 22 Jin Y, Yang H, Wang C. Org. Lett. 2020; 22: 2724
• 23 Tian Z.-X, Qiao J.-B, Xu G.-L, Pang X, Qi L, Ma W.-Y, Zhao Z.-Z, Duan J, Du Y.-F, Su P, Liu X.-Y, Shu X.-Z. J. Am. Chem. Soc. 2019; 141: 7637
• 24 He J, Xue Y, Han B, Zhang C, Wang Y, Zhu S. Angew. Chem. Int. Ed. 2020; 59: 2328
• 25 Anthony D, Lin Q, Baudet J, Diao T. Angew. Chem. Int. Ed. 2019; 58: 3198 ; corrigendum: Angew. Chem. Int. Ed. 2019, 58, 5157
• 26 Lan Y, Wang C. Commun. Chem. 2020; 3: 45
• 27 Fan P, Lan Y, Zhang C, Wang C. J. Am. Chem. Soc. 2020; 142: 2180
• 28 Tu H.-Y, Wang F, Huo L.-P, Li Y, Zhu S, Zhao X, Li H, Qing F.-L, Chu L. J. Am. Chem. Soc. 2020; 142: 9604
• 29 Tan Z, Wan X, Zang Z, Qian Q, Deng W, Gong H. Chem. Commun. 2014; 50: 3827
• 30a Majumdar KK, Cheng C.-H. Org. Lett. 2000; 2: 2295
• 30b Hu J.-X, Wu H, Li C.-Y, Sheng W.-J, Jia Y.-X, Gao J.-R. Chem. Eur. J. 2011; 17: 5234
• 30c Garcia KJ, Gilbert MM, Weix DJ. J. Am. Chem. Soc. 2019; 141: 1823
• 31 Zhou P, Xu T. Chem. Commun. 2020;