Stereoselective Synthesis of Z‐Vinyl Selenides Through the Reaction of Sodium Selenide with Organic Halides and Alkynes

A practical synthetic approach to the stereoselective synthesis of Z ‐vinyl selenides is described through the reaction of sodium selenide with organic halides, followed by the addition to alkynes. The reaction conditions were also successfully applied to the synthesis of selenochromones through the intramolecular version of this methodology by the reaction of 2‐chlorophenylynones with sodium selenide. The synthetic utility of vinyl selenides prepared was proven through the reaction with Kumada, Negishi and Suzuki substrates, giving the corresponding cross‐coupled products in good yields.