Ni-catalyzed hydroalkylation of olefins with N-sulfonyl amines

Xiao-Biao Yan, Lun Li, Wen-Qiang Wu, Lun Xu, Ke Li, Yu-Cheng Liu and Hang Shi ()
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Xiao-Biao Yan: Westlake University
Lun Li: Westlake University
Wen-Qiang Wu: Westlake University
Lun Xu: Westlake University
Ke Li: Westlake University
Yu-Cheng Liu: Westlake University
Hang Shi: Westlake University

Nature Communications, 2021, vol. 12, issue 1, 1-10

Abstract: Abstract Hydroalkylation, the direct addition of a C(sp3)–H bond across an olefin, is a desirable strategy to produce valuable, complex structural motifs in functional materials, pharmaceuticals, and natural products. Herein, we report a reliable method for accessing α-branched amines via nickel-catalyzed hydroalkylation reactions. Specifically, by using bis(cyclooctadiene)nickel (Ni(cod)2) together with a phosphine ligand, we achieved a formal C(sp3)–H bond insertion reaction between olefins and N-sulfonyl amines without the need for an external hydride source. The amine not only provides the alkyl motif but also delivers hydride to the olefin by means of a nickel-engaged β–hydride elimination/reductive elimination process. This method provides a platform for constructing chiral α-branched amines by using a P-chiral ligand, demonstrating its potential utility in organic synthesis. Notably, a sulfonamidyl boronate complex formed in situ under basic conditions promotes ring-opening of the azanickellacycle reaction intermediate, leading to a significant improvement of the catalytic efficiency.

Date: 2021
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DOI: 10.1038/s41467-021-26194-y

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