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A Chemoselective Reduction of Alkynes to (E)-Alkenes

Barry M. Trost,* Zachary T. Ball and Thomas Jöge

*Department of Chemistry, Stanford University, Stanford, California 94305-5080, Email:

B. M. Trost, Z. T. Ball, T. Joege, J. Am. Chem. Soc., 2002, 124, 7922-7923.

DOI: 10.1021/ja026457l


The hydrosilylation of alkynes using the ruthenium catalyst [Cp*Ru(MeCN)3]PF6 gives only (Z)-trans addition products. Subsequent protodesilylation of the crude vinylsilane products by the action of cuprous iodide and TBAF provides a general trans-alkyne reduction, which is compatible with many sensitive functional groups.

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Key Words

semireduction of alkynes

ID: J48-Y2002-1190