A Versatile C–H Functionalization of Tetrahydroisoquinolines Catalyzed by Iodine at Aerobic Conditions†

A versatile aerobic catalytic system (I(2) and O(2)/TBHP) for C-H functionalization is reported. This CDC (cross-dehydrogentive coupling) reaction is compatible with a large number of nucleophiles and is performed under ambient reaction conditions. The scope of the metal-free CDC is illustrated by synthesizing a variety of functionalized tetrahydroisoquinolines and N,N-dimethylaniline. The highlight of the method is a Friedel-Crafts reaction of phenols and indole with tertiary amines.