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All-Carbon-Substituted Vinylsilane Stable to TBAF:  Synthesis of Allyldimethylvinylsilane and Its Pd-Catalyzed Cross-Coupling under Mild Conditions

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journal contribution
posted on 17.08.2006 by Lianhai Li, Neenah Navasero
Allyldimethylvinylsilanes 3 are easily synthesized by the reaction of silylallylmetals, generated from 1 by n-BuLi/t-BuOK, with carbonyl compounds in the absence or presence of metal halides. They can tolerate 2 equiv of TBAF in THF at room temperature for at least 6 h but can be easily activated in the presence of a palladium catalyst and TBAF to perform the cross-coupling reaction with aryl iodides at room temperature.