Metal-Catalyzed\nHydrogen Atom Transfer (MHAT) Hydroalkylation\nwith Electron-Deficient Alkynes

We present a novel strategy for olefin construction via\nthe reductive\ncoupling of electron-neutral alkenes with electron-deficient alkynes\nunder metal-catalyzed hydrogen atom transfer conditions. This methodology\nprovides selective access to both <i>trans</i> and the more\nchallenging-to-synthesize <i>cis</i> isomers and permits\nthe olefin to be installed next to sterically hindered centers, key\nfactors in the synthesis of biologically active compounds. The reaction\nexhibits broad functional group tolerance and proceeds under mild,\nnontoxic conditions with high atom efficiency.