Copper-Catalyzed Cross-Coupling of Fluorinated Vinylstannanes with Organic Halides

β-stannylated propenoates 2 bearing a β-trifluoromethyl group, readily available by hydrostannation of 1, undergo copper(I) catalyzed coupling reactions without any palladium catalyst with allyl, benzyl, alkynyl, acyl and aryl halides. The corresponding adducts were obtained in moderate to good yields with a total retention of the double bond configuration. Interestingly, allyl bromides substituted with a stabilizing group did not led to expected coupling products but to the isomerization products 3. Thus, 31 examples are reported with yields up to 89 %. Finally, a mechanistic study was performed in order to confirm the mechanistic proposal.

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