4.8 Article

Silylacylation of Alkenes through N-Heterocyclic Carbene Catalysis

Journal

ORGANIC LETTERS
Volume 25, Issue 30, Pages 5579-5584

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c01840

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The construction of silicon-containing molecules has received attention in recent years. In this study, silyl radicals were generated through NHC catalysis under mild reaction conditions. This methodology offers a convenient route to a diverse range of β-silyl ketones with good functional group compatibility. The use of radical clock and electrochemical studies supports the hypothesis of ground-state SET, and a plausible mechanism for the organocatalytic transformation is proposed.
Theconstruction of silicon-containing molecules hasreceived increasingattention in recent years. Herein, we report the generation of silylradicals through NHC catalysis under mild reaction conditions. Thismethodology offers a novel and convenient route to a diverse rangeof & beta;-silyl ketones with a broad substrate scope and good functionalgroup compatibility. Both the radical clock and electrochemical studiesare consistent with the hypothesis of ground-state SET, and a plausiblemechanism for the organocatalytic transformation is proposed.

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