Nickel-Catalyzed Hydrogenation of Enamides and Quinolines via Photoinduced Hydrogen Atom Transfer

Radical hydrogenation facilitated by metal (Fe, Co, Mn, etc.) hydride-mediated hydrogen atom transfer (mHAT) has emerged as a powerful technique in organic synthesis. However, nickel-hydride (NiH) catalyzed radical hydrogenation has remained largely unexplored. Herein, we develop a NiH catalytic system that achieves the hydrogenation of enamides in high efficiency. This strategy stands out for its ability to hydrogenate challenging quinolines at room temperature, avoiding the catalyst poisoning and deactivation by quinolines and their hydrogenation products. Furthermore, the deuteration of alkenes was achieved with high deuteration rates (up to > 99%), underscoring its potential in the synthesis of deuterium-containing molecules.