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Visible-Light-Induced Palladium-Catalyzed Generation of Aryl Radicals from Aryl Triflates.

ABSTRACT: A mild visible-light-induced Pd-catalyzed intramolecular C-H arylation of amides is reported. The method operates by cleavage of a C(sp2 )-O bond, leading to hybrid aryl Pd-radical intermediates. The following 1,5-hydrogen atom translocation, intramolecular cyclization, and rearomatization steps lead to valuable oxindole and isoindoline-1-one motifs. Notably, this method provides access to products with readily enolizable functional groups that are incompatible with traditional Pd-catalyzed conditions.

SUBMITTER: Ratushnyy M

PROVIDER: S-EPMC7446712 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

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Visible-Light-Induced Palladium-Catalyzed Generation of Aryl Radicals from Aryl Triflates.

Ratushnyy Maxim M Kvasovs Nikita N Sarkar Sumon S Gevorgyan Vladimir V

Angewandte Chemie (International ed. in English) 20200406 26

A mild visible-light-induced Pd-catalyzed intramolecular C-H arylation of amides is reported. The method operates by cleavage of a C(sp<sup>2</sup> )-O bond, leading to hybrid aryl Pd-radical intermediates. The following 1,5-hydrogen atom translocation, intramolecular cyclization, and rearomatization steps lead to valuable oxindole and isoindoline-1-one motifs. Notably, this method provides access to products with readily enolizable functional groups that are incompatible with traditional Pd-cat ...[more]

PMID: 32155303

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