Tetrahedron letters

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

B Jiang, F Zhang, W Xiong

Index: Jiang, Biao; Zhang, Fangjiang; Xiong, Wennan Tetrahedron Letters, 2002 , vol. 43, # 4 p. 665 - 667

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Citation Number: 12

Abstract

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 stereoselectively, which underwent intramolecular cyclization in decalin at 190° C or in acetic acid with 1, 4- benzoquinone and sodium acetate to afford 3-trifluoromethyl-substituted furans in high ...