Friedel-Crafts Amidoalkylation via Thermolysis and Oxidative Photocatalysis

Friedel Crafts amidoalkylation was achieved by oxidation of dialkylamides using persulfate (S2O82-) in the presence of the visible light catalyst, Ru(bpy)(3)Cl-2, at room temperature, via a reactive N-acyliminium intermediate. Alternatively, mild heating of the dialkylamides and persulfate afforded a metal and Lewis acid-free Friedel-Crafts amidoalkylation. Alcohols and electron-rich arenes served as effective nucleophiles, forming new C-O or C-C bonds. In general, photocatalysis provided higher yields and better selectivities.