Alkyne Semihydrogenation with a Well-Defined Nonclassical Co-H2 Catalyst: A H2 Spin on Isomerization and E-Selectivity

J Am Chem Soc. 2016 Oct 19;138(41):13700-13705. doi: 10.1021/jacs.6b08128. Epub 2016 Oct 6.

Abstract

The reactivity of a CoI-H2 complex was extended toward the semihydrogenation of internal alkynes. Under ambient temperatures and moderate pressures of H2, a broad scope of alkynes were semihydrogenated using a CoI-N2 precatalyst, resulting in the formation of trans-alkene products. Furthermore, mechanistic studies using 1H, 2H, and para-hydrogen induced polarization (PHIP) transfer NMR spectroscopy revealed cis-hydrogenation of the alkyne occurs first. The Co-mediated alkene isomerization afforded the E-selective products from a broad group of alkynes with good yields and E/Z selectivity.