Synthesis of 3-Fluoroindoles via Photoredox Catalysis

Liubov I Panferova; Vladimir O Smirnov; Vitalij V Levin; Vladimir A Kokorekin; Marina I Struchkova; Alexander D Dilman

doi:10.1021/acs.joc.6b02344

Synthesis of 3-Fluoroindoles via Photoredox Catalysis

J Org Chem. 2017 Jan 6;82(1):745-753. doi: 10.1021/acs.joc.6b02344. Epub 2016 Dec 27.

Authors

Liubov I Panferova¹, Vladimir O Smirnov¹, Vitalij V Levin¹, Vladimir A Kokorekin^{1

2}, Marina I Struchkova¹, Alexander D Dilman¹

Affiliations

¹ N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences , Leninsky prosp. 47, 119991 Moscow, Russian Federation.
² First I. M. Sechenov Moscow State Medical University , Trubetskaya st. 8-2, 119991 Moscow, Russian Federation.

PMID: 27943669
DOI: 10.1021/acs.joc.6b02344

Abstract

A method for the synthesis of 3-fluoroindoles from N-arylamines substituted with the CF₂I group is described. The reaction is mediated by a ruthenium photocatalyst 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.

Publication types

Research Support, Non-U.S. Gov't