Metal-Catalyzed Hydrogen Atom Transfer (MHAT) Hydroalkylation with Electron-Deficient Alkynes

We present a novel strategy for olefin construction via
the reductive
coupling of electron-neutral alkenes with electron-deficient alkynes
under metal-catalyzed hydrogen atom transfer conditions. This methodology
provides selective access to both trans and the more
challenging-to-synthesize cis isomers and permits
the olefin to be installed next to sterically hindered centers, key
factors in the synthesis of biologically active compounds. The reaction
exhibits broad functional group tolerance and proceeds under mild,
nontoxic conditions with high atom efficiency.