Preparation of α- or β-trifluoromethylated vinylstannanes and their cross-coupling reactions |
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Authors: | In Howa Jeong Young Sam Park Myong Sang Kim Yong Sup Song |
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Affiliation: | Department of Chemistry, Yonsei University, Wonju 220-710, South Korea |
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Abstract: | α- or β-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. |
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Keywords: | Trifluoromethylated vinylstannane Cross-coupling reaction Arylation reaction Acylation reaction |
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