A Chemoselective Reduction of Alkynes to (E)-Alkenes

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Abstract
The trans reduction of all types of alkynes to give (E)-olefins is achieved through a two-stage trans hydrosilylation and protodesilylation. Reaction of an alkyne and a silane with the ruthenium catalyst [Cp*Ru(MeCN)3]PF6 results in clean hydrosilylation to give only the (Z)-trans addition product at ambient temperature with catalyst loadings of 1−5 mol %. The crude vinylsilane products are then protodesilylated by the action of cuprous iodide and TBAF at rt−35 °C. The reaction is compatible with many sensitive functional groups and provides a general trans-alkyne reduction not possible by other means.