Copper Photoredox Catalyzed A3′ Coupling of Arylamines, Terminal Alkynes, and Alcohols through a Hydrogen Atom Transfer Process

The first successful example of the three-component coupling of N-alkylanilines, terminal alkynes, and alcohols was achieved at room temperature by a visible-light-mediated copper-catalyzed photoredox hydrogen-atom transfer process. This method allows preparation of propargylamines through uniquely selective alpha-C-H bond activation of unactivated alkylalcohols. Preliminary studies indicate that formation of alpha-oxy radical is operative. This approach facilitates rapid access to biologically important propargylamines from methanol as an abundant feedstock.