Nitrogenation and Oxygenation of an Unstrained C-C Bond Enabled by the Merger of Visible-Light and Cu-Catalysis

Unstrained carbon-carbon bonds are among the most prevalent and inert chemical bonds. Thus, developing synthetic transformations directly from unstrained carbon-carbon bonds under mild conditions is ideal yet challenging due to the inertness and steric hindrance. Here, a visible-light and copper-catalyzed azidation and etherification of a remote and unstrained C-C bond of amines via 1,4-aryl migration have been reported. This redox-neutral protocol shows exquisite site-selectivity, broad scope, and good functional group tolerance, directly transforming unstrained C-C bonds to C-N and C-O bonds at room temperature. Facile derivatizations of benzyl azide products into free amines, triazoles, and phosphamides highlight the potential utility of this method for target molecule synthesis and medicinal chemistry.