All-carbon-substituted vinylsilane stable to TBAF: synthesis of allyldimethylvinylsilane and its Pd-catalyzed cross-coupling under mild conditions.
[reaction: see text] 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.
Li
Lianhai
L
Department of Medicinal Chemistry, Merck Frosst Centre for Therapeutic Research, P.O. Box 1005, Pointe-Claire-Dorval, Quebec, Canada H9R 4P8. lianhai_li@merck.com
Navasero
Neenah
N