Reductive Cleavage of C(sp2)–CF3Bonds in Trifluoromethylpyridines

Autor: St. Onge, Piers, Khan, Shajia I., Cook, Adam, Newman, Stephen G.
Zdroj: Organic Letters; February 2023, Vol. 25 Issue: 6 p1030-1034, 5p
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(sp2)–CF3groups 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: Supplemental Index