Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Palladium-Catalyzed Carbonylative Coupling of Tributyl(1-fluorovinyl)stannane with Aryl Halides and Aryl Triflates
Takeshi HanamotoKumiko HandaTomonori Mido
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2002 Volume 75 Issue 11 Pages 2497-2502

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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.

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© 2002 The Chemical Society of Japan
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