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Redox-Neutral Cross-Coupling Amination with Weak N-Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines, Carbamates, and Imines via Nickelaelectrocatalysis.

ABSTRACT: A nickel-catalyzed cross-coupling amination with weak nitrogen nucleophiles is described. Aryl halides as well as aryl tosylates can be efficiently coupled with a series of weak N-nucleophiles, including anilines, sulfonamides, sulfoximines, carbamates, and imines via concerted paired electrolysis. Notably, electron-deficient anilines and sulfonamides are also suitable substrates. Interestingly, when benzophenone imine is applied in the arylation, the product selectivity toward the formation of amine and imine product can be addressed by a base switch. In addition, the alternating current mode can be successfully applied. DFT calculations support a facilitated reductive elimination pathway.

SUBMITTER: Zhu C

PROVIDER: S-EPMC8395614 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Redox-Neutral Cross-Coupling Amination with Weak <i>N-</i>Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines, Carbamates, and Imines via Nickelaelectrocatalysis.

Zhu Chen C Kale Ajit Prabhakar AP Yue Huifeng H Rueping Magnus M

JACS Au 20210615 7

A nickel-catalyzed cross-coupling amination with weak nitrogen nucleophiles is described. Aryl halides as well as aryl tosylates can be efficiently coupled with a series of weak <i>N-</i>nucleophiles, including anilines, sulfonamides, sulfoximines, carbamates, and imines via concerted paired electrolysis. Notably, electron-deficient anilines and sulfonamides are also suitable substrates. Interestingly, when benzophenone imine is applied in the arylation, the product selectivity toward the format ...[more]

PMID: 34467349

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