1-Halogenoalk-1-ynes upon hydroboration with dialkylborane followed by treatment with copper(II) halides in the presence of a small amount of water in polar aprotic solvents give both mixed 1,1-dihalogenoalk-1-enes of defined stereochemistry and single isomers in reasonable yield.
Y. Masuda, T. Suyama, M. Murata and S. Watanabe, J. Chem. Soc., Perkin Trans. 1, 1995, 2955 DOI: 10.1039/P19950002955
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