The regio- and stereoselective addition of carbon nucleophiles to trifluoromethyl phenylsulfanyl acetylene: a novel and expeditious approach to 3-trifluoromethyl furans

A convenient generation of trifluoromethyl phenylsulfanyl acetylene was realized from 2-bromo-1-phenylsulfanyl-3,3,3-trifluoropropene. The reagent was reacted with carbanions to give (1E,3E)-2-trifluoromethylbutadienyl phenyl sulfides regio- and stereo selectively, which underwent intramolecular cyclization in decalin at 190degreesC or in acetic acid with 1,4-benzoquinone and sodium acetate to afford 3-trifluoromethyl-substituted furans in high yields. (C) 2002 Elsevier Science Ltd. All rights reserved.