1.11 Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions

Abstract

Nickel-catalyzed enantioselective reductive cross-coupling reactions enable simple and efficient synthesis of enantioenriched compounds, with high functionality tolerance, through circumventing the use of pregenerated organometallics. In this chapter, the most quintessential examples of the recent advances in this field have been summarized, and the contents are organized according to the reaction types.

Schlüsselwörter

nickel catalysis - reductive cross coupling - cross-electrophile coupling - asymmetric catalysis - ring-opening reactions - dicarbofunctionalization - Heck reaction - arylation - alkylation - carbamoylation - acylation - vinylation - organohalides - epoxides - aziridines - cyclobutanones - alkenes - oxindoles - indanes - indanones

• 1 Everson DA, Weix DJ. J. Org. Chem. 2014; 79: 4793

• 2 Moragas T, Correa A, Martin R. Chem.–Eur. J. 2014; 20: 8242

• 3 Gu J, Wang X, Xue W, Gong H. Org. Chem. Front. 2015; 2: 1411

• 4 Weix DJ. Acc. Chem. Res. 2015; 48: 1767

• 5 Richmond E, Moran J. Synthesis 2018; 50: 499

• 6 Poremba KE, Dibrell SE, Reisman SE. ACS Catal. 2020; 10: 8237

• 7 Jin Y, Wang C. Synlett 2020; 31: 1843

• 8 Cherney AH, Kadunce NT, Reisman SE. J. Am. Chem. Soc. 2013; 135: 7442

• 9 Cherney AH, Reisman SE. J. Am. Chem. Soc. 2014; 136: 14365

• 10 Hofstra JL, Cherney AH, Ordner CM, Reisman SE. J. Am. Chem. Soc. 2018; 140: 139

• 11 Poremba KE, Kadunce NT, Suzuki N, Cherney AH, Reisman SE. J. Am. Chem. Soc. 2017; 139: 5684

• 12 Suzuki N, Hofstra JL, Poremba KE, Reisman SE. Org. Lett. 2017; 19: 2150

• 13 Kadunce NT, Reisman SE. J. Am. Chem. Soc. 2015; 137: 10480

• 14 Guan H, Zhang Q, Walsh PJ, Mao J. Angew. Chem. Int. Ed. 2020; 59: 5172

• 15 Lau SH, Borden MA, Steiman TJ, Wang LS, Parasram M, Doyle AG. J. Am. Chem. Soc. 2021; 143: 15873

• 16 Woods BP, Orlandi M, Huang C.-Y, Sigman MS, Doyle AG. J. Am. Chem. Soc. 2017; 139: 5688

• 17 Ding D, Dong H, Wang C. iScience 2020; 23: 101017

• 18 Wang K, Ding Z, Zhou Z, Kong W. J. Am. Chem. Soc. 2018; 140: 12364

• 19 Jin Y, Wang C. Angew. Chem. Int. Ed. 2019; 58: 6722

• 20 Jin Y, Yang H, Wang C. Org. Lett. 2020; 22: 2724

• 21 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

• 22 Qiao J.-B, Zhang Y.-Q, Yao Q.-W, Zhao Z.-Z, Peng X, Shu X.-Z. J. Am. Chem. Soc. 2021; 143: 12961

• 23 Lan Y, Wang C. Commun. Chem. 2020; 3: 45

• 24 Wu X, Qu J, Chen Y. J. Am. Chem. Soc. 2020; 142: 15654

• 25 Anthony D, Lin Q, Baudet J, Diao T. Angew. Chem. Int. Ed. 2019; 58: 3198

• 26 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

• 27 Wei X, Shu W, García-Domínguez A, Merino E, Nevado C. J. Am. Chem. Soc. 2020; 142: 13515