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Catalytic Anti-Markovnikov Hydrobromination of Alkynes

Mycah R. Uehling, Richard P. Rucker and Gojko Lalic*

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

M. R. Uehling, R. P. Rucker, G. Lalic, J. Am. Chem. Soc., 2014, 136, 8799-8803.

DOI: 10.1021/ja503944n (free Supporting Information)


Abstract

A catalytic anti-Markovnikov hydrobromination of aryl- and alkyl-substituted terminal alkynes affords terminal E-alkenyl bromides in high yield and with excellent regio- and diastereoselectivity. The reaction conditions are compatible with a wide range of functional groups, including esters, nitriles, epoxides, aryl boronic esters, terminal alkenes, silyl ethers, aryl halides, and alkyl halides.

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Key Words

alkenyl bromides, diphenylsilane


ID: J48-Y2014