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Direct Approach to N-Substituted-2-Fluoroindoles by Sequential Construction of C–N Bonds from gem-Difluorostyrenes

Author:
Zhang, Bin, Zhang, Xiaofei, Hao, Jian, Yang, Chunhao
Source:
Organic letters 2017 v.19 no.7 pp. 1780-1783
ISSN:
1523-7052
Subject:
Lewis bases, chemical bonding, chemical reactions, chemical structure, organic compounds
Abstract:
A mild and efficient synthesis of N-substituted-2-fluoroindole derivatives was achieved via Buchwald–Hartwig couplings and a sequential, base-promoted intramolecular nucleophilic reaction−β-fluorine elimination. By employing easily obtained gem-difluorostyrenes and primary arylamines, the scope, advantages, and limitations of this reaction were well investigated. Furthermore, this strategy distinguishes itself by high modularity, operational simplicity, and a wide substrate scope, giving rise to a broad array of 2-fluoroindole derivatives in moderate to excellent yields.
Agid:
5793910