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Radical Cation Cycloadditions Using Cleavable Redox Auxiliaries.

ABSTRACT: The incorporation of an easily oxidized arylsulfide moiety facilitates the photocatalytic generation of alkene radical cations that undergo a variety of cycloaddition reactions with electron-rich reaction partners. The sulfide moiety can subsequently be reductively cleaved in a traceless fashion, affording products that are not otherwise directly accessible using photoredox catalysis. This approach constitutes a novel oxidative "redox auxiliary" strategy that offers a practical means to circumvent a fundamental thermodynamic limitation facing photoredox reactions.

SUBMITTER: Lin S

PROVIDER: S-EPMC5287351 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature

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Radical Cation Cycloadditions Using Cleavable Redox Auxiliaries.

Lin Shishi S Lies Shane D SD Gravatt Christopher S CS Yoon Tehshik P TP

Organic letters 20161229 2

The incorporation of an easily oxidized arylsulfide moiety facilitates the photocatalytic generation of alkene radical cations that undergo a variety of cycloaddition reactions with electron-rich reaction partners. The sulfide moiety can subsequently be reductively cleaved in a traceless fashion, affording products that are not otherwise directly accessible using photoredox catalysis. This approach constitutes a novel oxidative "redox auxiliary" strategy that offers a practical means to circumve ...[more]

PMID: 28032508

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