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: lalicchem.washington.edu
M. T. Lee, M. G. Goodstein, G. Lalic, J. Am. Chem. Soc., 2019, 141, 17086-17091.
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.
see article for more examples
proposed catalytic cycle