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Three-component reductive conjugate addition/aldol tandem reaction enabled by nickel/photoredox dual catalysis.

ABSTRACT: A three-component reductive cross-coupling of aryl halides, aldehydes, and alkenes by nickel/photoredox dual catalysis is disclosed. The key to success for this tandem transformation is to identify α-silylamine as a unique organic reductant, which releases silylium ions instead of protons to prevent unwanted protonation processes, and meanwhile serves as Lewis acid to activate aldehydes in situ. This dual catalytic protocol completes a traditional conjugate addition/aldol sequence that eliminates the requirement of organometallic reagents and metal-based reductants, thus providing a mild synthetic route to highly valuable β-hydroxyl carbonyl compounds with contiguous 1,2-stereocenters.

SUBMITTER: Zhao H

PROVIDER: S-EPMC9906790 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature

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Three-component reductive conjugate addition/aldol tandem reaction enabled by nickel/photoredox dual catalysis.

Zhao Hongping H Yuan Weiming W

Chemical science 20230110 6

A three-component reductive cross-coupling of aryl halides, aldehydes, and alkenes by nickel/photoredox dual catalysis is disclosed. The key to success for this tandem transformation is to identify α-silylamine as a unique organic reductant, which releases silylium ions instead of protons to prevent unwanted protonation processes, and meanwhile serves as Lewis acid to activate aldehydes <i>in situ</i>. This dual catalytic protocol completes a traditional conjugate addition/aldol sequence that el ...[more]

PMID: 36794187

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