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Updated: Jan 27, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Dearomatization-Rearomatization Strategy for Reductive Cross-Coupling of Indoles with Ketones in Water
Zemin Wang1, Huiying Zeng1, Chao-Jun Li2
1The State Key Laboratory of Applied Organic Chemistry , Lanzhou University , 222 Tianshui Road , Lanzhou 730000 , People's Republic of China.
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.
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