Copper Photoredox Catalyzed A3’ Coupling of Arylamines, Terminal Alkynes, and Alcohols via a HAT 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 a-C@H bond activation of unactivated alkylalcohols. Preliminary studies indicate that formation of a-oxy radical is operative. This approach facilitates rapid access to biologically important propargylamines from methanol as an abundant feedstock.