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Diastereodivergent Reductive Cross Coupling of Alkynes through Tandem Catalysis: Z- and E-Selective Hydroarylation of Terminal Alkynes

Megan K. Armstrong, Madison B. Goodstein, Gojko Lalic*

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

M. K. Armstrong, M. B. Goodstein, G. Lalic, J. Am. Chem. Soc., 2018, 140, 10233-10241.

DOI: 10.1021/jacs.8b05113 (free Supporting Information)


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Abstract

A diastereodivergent hydroarylation of terminal alkynes allows highly selective synthesis of both E and Z diastereoisomers of aryl alkenes, from the same set of starting materials, using the same combination of palladium and copper catalysts. The selectivity is controlled by the stoichiometry of the alcohol additive. The reactions tolerates esters, nitriles, alkyl halides, epoxides, carbamates, acetals, ethers, silyl ethers, and thioethers.


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Key Words

Sonogashira coupling, olefination, silanes


ID: J48-Y2018