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Synthesis of Isomerically Pure (Z)-Alkenes from Terminal Alkynes and Terminal Alkenes: Silver-Catalyzed Hydroalkylation of Alkynes

Mitchell T. Lee, Madison B. Goodstein, and Gojko Lalic*

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

M. T. Lee, M. G. Goodstein, G. Lalic, J. Am. Chem. Soc., 2019, 141, 17086-17091.

DOI: 10.1021/jacs.9b09336


A silver-catalyzed hydroalkylation of terminal alkynes with alkylboranes as coupling partners enables an efficient synthesis of diastereopure Z-alkenes (Z:E > 300:1). This method offers a broad functional group compatibility. A 1,2-metalate rearrangement of the silver borate intermediate is the key step responsible for the stereochemical outcome of the reaction.

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proposed catalytic cycle

Key Words


ID: J48-Y2019