Redox-Neutral Cross-Coupling Amination with Weak N-Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines, Carbamates, and Imines via Nickelaelectrocatalysis
KAUST DepartmentKAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), Thuwal 23955-6900, Saudi Arabia
Chemical Science Program
Permanent link to this recordhttp://hdl.handle.net/10754/669682
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AbstractA 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.
CitationZhu, C., Kale, A. P., Yue, H., & Rueping, M. (2021). Redox-Neutral Cross-Coupling Amination with Weak N-Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines, Carbamates, and Imines via Nickelaelectrocatalysis. JACS Au. doi:10.1021/jacsau.1c00148
SponsorsC.Z. acknowledges King Abdullah University of Science and Technology (KAUST) for support and the KAUST Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II. This work was financially supported by KAUST, Saudi Arabia, Office of Sponsored Research.
PublisherAmerican Chemical Society (ACS)
Except where otherwise noted, this item's license is described as This document is the Accepted Manuscript version of a Published Work that appeared in final form in JACS Au, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/jacsau.1c00148.