Synthesis of 3-Fluoroindoles via Photoredox Catalysis

Liubov I. Panferova, Vladimir O. Smirnov, Vitalij V. Levin, Vladimir A. Kokorekin, Marina I. Struchkova and Alexander D. Dilman*

*N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russian Federation, Email: adil25mail.ru

L. I. Panferova, V. O. Smirnov, V. V. Levin, V. K. Kokorekin, M. I. Struchkova, A. D. Dilman, J. Org. Chem., 2017, 82, 745-753.

DOI: 10.1021/acs.joc.6b02344

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Abstract

A ruthenium photocatalyst mediates a synthesis of 3-fluoroindoles from N-arylamines substituted with the CF₂I group in the presence of a substoichiometric amount of triphenylphosphine upon irradiation with blue light. The starting N-arylamines are readily obtained by nucleophilic iododifluoromethylation of iminium ions.

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proposed mechanism

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Key Words

indoles

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ID: J42-Y2017