Preparation of Allyl and Vinyl Silanes by the Palladium-Catalyzed Silylation of Terminal Olefins: A Silyl-Heck Reaction


  • We acknowledge the University of Delaware (UD) for research support and the following sources for fellowships: NIH/NIGMS CBI Program (5T32 GM 08550-16, SESM); David Plastino and the ACS SURF Program (DTA); HHMI Grant 52006947 to the University of Delaware, and the UD NUCLEUS Program (KAJ). Data were acquired on instruments obtained through NSF and NIH funding (NSF MIR 0421224 & CRIF MU CHE0840401, NIH P20 RR017716).


original image

Installing silicon is easy! A high-yielding protocol for the palladium-catalyzed silylation of terminal alkenes is reported. This method allows facile conversion of styrenes to E-β-silyl styrenes by using iodotrimethylsilane (TMSI) or chlorotrimethylsilane/lithium iodide (see scheme). Terminal allyl silanes with good E/Z ratios are also readily accessed from α-olefins.