A high-yielding protocol for the palladium-catalyzed silylation of terminal alkenes using silyl halides is reported. This method allows facile conversion of styrenes to E-(�)-silyl styrenes by using iodotrimethylsilane or chlorotrimethylsilane/ lithium iodide. Terminal allyl silanes with good E/Z ratios are also readily accessed from a-olefins. We believe these reactions proceed through a Heck-type mechanism. When combined with existing technology, this transformation provides a powerful strategy to selectively functionalize the vinyl or allylic position of terminal alkenes.

Preparation of allyl and vinyl silanes by the palladium-catalyzed silylation of terminal olefins: A silyl-Heck reaction

244th National Meeting (2012)

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