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

Autor:	St Onge P; Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada., Khan SI; Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada., Cook A; Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada., Newman SG; Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2023 Feb 17; Vol. 25 (6), pp. 1030-1034. Date of Electronic Publication: 2023 Feb 07.
DOI:	10.1021/acs.orglett.3c00258
Abstrakt:	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.
Databáze:	MEDLINE
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