Palladium-Catalyzed Carbonylative Coupling of Tributyl(1-fluorovinyl)stannane with Aryl Halides and Aryl Triflates

Abstract

Abstract We have found that tributyl(1-fluorovinyl)stannane (2) could be readily prepared from the reaction of (1-fluorovinyl)methyldiphenylsilane1 (1) and bis(tributyltin) oxide in the presence of a catalytic amount of CsF in DMF in good yields. The palladium-catalyzed carbonylative cross-coupling reaction of 2 with aryl iodides bearing various functional groups smoothly proceeded giving the corresponding aryl 1-fluorovinyl ketones in good yields under an atmospheric pressure of carbon monoxide. A similar carbonylative cross-coupling reaction of 2 with aryl triflates was also accomplished in the presence of tetrabutylammonium iodide (Bu4NI) as an additive.