Regio- and stereoselective synthesis of tetrasubstituted ( E )-(2-chloro-2-fluoro-1-iodovinyl)dimethylphenylsilane and its desilylative sonogashira coupling.

Trihalo-substituted vinylsilane was readily synthesized in 77% yield and in an excellent regio- and stereoselective manner from in situ -generated fluorosilylacetylene, followed by the addition of I 2 and NCS. The silane was committed to sequential Sonogashira coupling with various terminal acetylenes under mild conditions, affording desilylated chlorofluoro-enyne adducts in moderate to good yields.