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Additions of Aldehyde-Derived Radicals and Nucleophilic N-Alkylindoles to Styrenes by Photoredox Catalysis.

ABSTRACT: The consecutive addition of acyl radicals and N-alkylindole nucleophiles to styrenes was established, as well as some additional radical-nucleophile combinations. Both aryl and aliphatic aldehydes give reasonable yields. The reaction proceeds best for α-substituted styrenes, effectively creating a quaternary all-carbon center. Some iridium-based photoredox systems are catalytically active; furthermore, a base is needed in this transformation. Radicals are formed by reductive perester cleavage and hydrogen atom transfer.

SUBMITTER: Lux M

PROVIDER: S-EPMC7304929 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Additions of Aldehyde-Derived Radicals and Nucleophilic <i>N</i>-Alkylindoles to Styrenes by Photoredox Catalysis.

Lux Marcel M Klussmann Martin M

Organic letters 20200414 9

The consecutive addition of acyl radicals and <i>N</i>-alkylindole nucleophiles to styrenes was established, as well as some additional radical-nucleophile combinations. Both aryl and aliphatic aldehydes give reasonable yields. The reaction proceeds best for α-substituted styrenes, effectively creating a quaternary all-carbon center. Some iridium-based photoredox systems are catalytically active; furthermore, a base is needed in this transformation. Radicals are formed by reductive perester clea ...[more]

PMID: 32286834

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