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Visible‐Light‐Induced Palladium‐Catalyzed Generation of Aryl Radicals from Aryl Triflates
Author(s) -
Ratushnyy Maxim,
Kvasovs Nikita,
Sarkar Sumon,
Gevorgyan Vladimir
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201915962
Subject(s) - intramolecular force , isoindoline , chemistry , aryl , palladium , catalysis , radical , oxindole , photochemistry , bond cleavage , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , alkyl
A mild visible‐light‐induced Pd‐catalyzed intramolecular C−H arylation of amides is reported. The method operates by cleavage of a C(sp 2 )−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.