Issue 26, 2021

Mechanistic insights into Ni-catalyzed hydrogen atom transfer (HAT)-triggered hydrodefluorination of CF3-substituted alkenes

Abstract

We report the first computational study on a nickel hydride HAT-initiated catalytic reaction, a novel hydrodefluorination of CF3-substituted aryl alkenes to afford gem-difluoroalkenes. This study provides detailed mechanistic insights into the reaction, including HAT from NiH to C[double bond, length as m-dash]C, a carbon radical rebound to nickel to facilitate chemoselective defluorination, and a two-state reactivity of Ni(II) enabling σ-bond metathesis with PhSiH3 to regenerate the catalyst. The findings can have implications for developing new metal hydride HAT-initiated reactions.

Graphical abstract: Mechanistic insights into Ni-catalyzed hydrogen atom transfer (HAT)-triggered hydrodefluorination of CF3-substituted alkenes

Supplementary files

Article information

Article type
Communication
Submitted
02 Jun 2021
Accepted
08 Jun 2021
First published
08 Jun 2021

Dalton Trans., 2021,50, 9026-9030

Mechanistic insights into Ni-catalyzed hydrogen atom transfer (HAT)-triggered hydrodefluorination of CF3-substituted alkenes

J. Guo, D. Zhang and X. Wang, Dalton Trans., 2021, 50, 9026 DOI: 10.1039/D1DT01799C

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