Metal-catalyzed Markovnikov-type selective hydrofunctionalization of terminal alkynes.

Metal-catalyzed highly Markovnikov-type selective hydrofunctionalization of terminal alkynes provides a straightforward and atom-economical route to access 1,1-disubstituted alkenes, which have a wide range of applications in organic synthesis. However, the highly Markovnikov-type selective transformations are challenging due to the electronic and steric effects during the addition process. With the development of metal-catalyzed organic synthesis, different metal catalysts have been developed to solve this challenge, especially for platinum group metal catalysts. In this perspective, we review homogeneous metal-catalyzed Markovnikov-type selective hydrofunctionalization of terminal alkynes according to the classified element types as well as reaction mechanisms. Future avenues for investigation are also presented to help expand this exciting field.