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Reductive Cleavage of C(sp 2 )-CF 3 Bonds in Trifluoromethylpyridines.

Piers St OngeShajia I KhanAdam CookStephen G Newman
Published in: Organic letters (2023)
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(sp 2 )-CF 3 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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