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Updated: Sep 2, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
AlCl3-Mediated CHF2 Transfer and Cyclocondensation of Difluoromethoxy Functionalized o-Phenylenediamines to Access
Vinothkumar Vinayagam1, Satish Kumar Karre1, Sreenivasa Reddy Kasu1
1Curia India Pvt. Ltd (Formerly Albany Molecular Research, Hyderabad Research Centre), MN Park, Genome Valley, Shameerpet, RR District, Hyderabad 500078, India.
Abstract:
Herein, we report for the first time a transition-metal-free frustrated Lewis pair (FLP) catalyzed CHF2 group migration from an oxygen atom to the neighboring nitrogen atom, which led to the synthesis of N-substituted benzimidazoles at room temperature with excellent yields, broad functional group tolerance, and a short reaction time. The oxygen-attached difluoromethane acted as a C1 source in the synthesis of N-substituted benzimidazoles in the presence of AlCl3 by cleaving one C-O bond and two C-F bonds, resulting in formation of two new C-N bonds.
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