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Dearomatization–Rearomatization Strategy for Reductive Cross-Coupling of Indoles with Ketones in Water

Author:
Wang, Zemin, Zeng, Huiying, Li, Chao-Jun
Source:
Organic letters 2019 v.21 no.7 pp. 2302-2306
ISSN:
1523-7052
Subject:
Lewis acids, Lewis bases, alkylation, cross-coupling reactions, indoles, ketones, moieties, nitrogen
Abstract:
N-Alkylation of indoles is one of the important pathways for the construction of various biologically active indole molecules. Using ketones as N-alkylation reagent for indoles has been a great challenge not only because of the competing alkylation reaction of C-3 position but also because of the poor nucleophilicity of the nitrogen atom of indole, in addition to the steric hindrance and lower electrophilicity of the ketones. A dearomatization–rearomatization strategy has been developed for reductive cross-coupling of indoles with ketones in water. Various functional groups and other heterocyclic compounds are tolerated.
Agid:
6363100