Regioselective transformation of alkynes catalyzed by a copper hydride or boryl copper species

This review summarizes the transformation of alkynes using a copper hydride (Cu-H) or boryl copper (Cu-B) species as the active species. The semihydrogenation, hydrocarboxylation, and hydroboration of alkynes have been developed using Cu-H as the active species. The hydroboration, diboration, carboboration and boracarboxylation of alkynes involve the Cu-B species. These transformations afforded multi-substituted alkenes that are potentially good intermediates in organic synthesis. The key to the regioselective transformation is the addition of the Cu-H or Cu-B species to an alkyne, to afford the corresponding alkenylcopper intermediate regioselectively.