Research Progress in Metal-Catalyzed Addition of Carbon-Hetero Bonds to Alkynes

The addition of carbon-hetero bonds to alkynes has become an important apporach for the functionalization of carbon-carbon triple bonds. It can construct two bonds, namely one carbon-carbon bond and one carbon-hetero bond, in a single one step. These addition reactions feature high efficiency and high atom-economy. In recent years, metal-catalyzed (Al, Fe, Ni, Cu, Ga, Ru, Rh, Pd, Hf, Ir, Pt, Au, Bi, etc.) addition of many various kinds of carbon-hetero bonds to alkynes has achieved lots of important developments. According to the types of carbon-hetero bonds, the addition of 8 different kinds of carbon-hetero bonds [C-H, C-B, C-N, C-O, C-Si, C-S, C-X (X=Cl, Br, I), C-Se] to alkynes is reviewed in this paper, and the reaction conditions, reaction selectivities (regioselectivities and stereoselectivities) and reaction mechanisms are also discussed and summarized.