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.