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Stereospecific Synthesis of E-Alkenes through Anti-Markovnikov Hydroalkylation of Terminal Alkynes

Avijit Hazra, Jason Chen, Gojko Lalic*

*University of Washington, Seattle, Washington 98103, United States, Email:

A. Hazra, J. Chen, G. Lalic, J. Am. Chem. Soc., 2019, 141, 12464-12469.

DOI: 10.1021/jacs.9b04800


The cooperative action of copper and nickel catalysts enables a stereospecific hydroalkylation of terminal alkynes with alkyl iodides to provide E-alkenes with excellent anti-Markovnikov selectivity. The reaction can be accomplished in the presence of esters, nitriles, aryl bromides, ethers, alkyl chlorides, anilines, and a wide range of nitrogen-containing heteroaromatic compounds.

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Key Words

alkenes, triphenylsilane

ID: J48-Y2019