Copper-Catalyzed Hydroalkylation of Terminal Alkynes

Mycah R. Uehling, Alison M. Suess and Gojko Lalic*

*The Department of Chemistry, University of Washington, Seattle, Washington 98195, United States, Email: lalicchem.washington.edu

M. R. Uehling, A. M. Suess, G. Lalic, J. Am. Chem. Soc., 2015, 137, 1424-1427.

DOI: 10.1021/ja5124368

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Abstract

A copper-catalyzed hydroalkylation of terminal alkynes using alkyl triflates as coupling partners and (Me₂HSi)₂O as a hydride donor proceeds with excellent anti-Markovnikov regioselectivity and provides exclusively (E)-alkenes. Both alkyl- and aryl-substituted alkynes can be used as substrates, together with 1° alkyl and benzylic triflates. Finally, the transformation can be accomplished in the presence of a wide range of functional groups.

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Key Words

alkenes, silanes

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ID: J48-Y2015