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Updated: Aug 11, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Reductive Cleavage of C(sp2)-CF3 Bonds in Trifluoromethylpyridines
Piers St Onge1, Shajia I Khan1, Adam Cook1
1Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada.
Abstract:
A reductive detrifluoromethylation protocol has been developed making use of an earth-abundant alkoxide base and silicon hydride species. A variety of pyridine and quinoline substrates bearing alkyl, aryl, and amino functional groups are reduced in moderate to high yields. The reaction is chemoselective for C(sp2)-CF3 groups located at the 2-position on the pyridine ring, leaving trifluoromethyl groups located elsewhere on the molecule intact. Preliminary mechanistic studies demonstrate that the combination of silane and base generates a strongly reducing system that may transfer an electron to electron-deficient π systems.
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