Copper(I)-catalyzed formal carboboration of alkynes: Synthesis of tri- and tetrasubstituted vinylboronates

Article abstract of DOI:10.1021/ja307670k

The first copper-catalyzed formal carboboration of alkynes, in which a C-B bond and a C-C bond are created in a single catalytic cycle, is presented. The reaction proceeds with high regioselectivity and syn-stereoselectivity to form tri- and tetrasubstituted vinylboronic esters from commercially available bis(pinacolato)diboron. A subsequent cross-coupling reaction gives access to highly substituted alkenes.