Oxidative cross-coupling of vinylsilanes in water

Palladium-promoted cross-dimerization reaction of alkenylsilanes is reported for the first time, which is also one of the very first studies on oxidative cross-coupling between vinylic organometallic reagents. The reaction occurs at room temperature in aqueous micelles and represents a convenient access to all-trans push–pull butadienes.

Graphical abstractThe first investigation of palladium-catalyzed oxidative cross-coupling reaction of vinylsilanes bearing substituents with complementary electronic effects is reported. Besides being the first example on oxidative cross-coupling of vinylic organosilicon reagents, the protocol is a convenient access to push–pull butadienes.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► One of the very first examples of oxidative cross-coupling between vinyl organometallic reagents. ► Alkenyl silanes as useful synthetic intermediates to access extended polyenic systems. ► A suitable approach to the synthesis of unsymmetrically substituted push–pull butadienes.