Preparation of α- or β-trifluoromethylated vinylstannanes and their cross-coupling reactions

alpha- or beta-Trifluoromethylated vinylstannanes 1, 2a, 3 and 4 were prepared form 1,1-bis(phenylthio)-2,2,3,3,3-pentafluoropropylbenzene (5) via several steps. The cross-coupling arylation reactions of 1-4 with aryl iodides bearing a bromo, methoxy, methyl, nitro or trifluoromethyl group on para- or meta-position of benzene ring afforded the corresponding coupling products in good yields. Compounds 1, 2a and 4 underwent the acylation reaction with various types of acyl chlorides to give the corresponding trifluoromethylated enone derivatives in good yields. Reduction of trifluoromethylated enone derivatives with LiAlH4, followed by Fridel-Craft's type of cyclization with AlCl3 provided trifluoromethylated indene derivatives in good yields. (C) 2002 Elsevier Science B.V. All rights reserved.