A versatile C-H functionalization of tetrahydroisoquinolines catalyzed by iodine at aerobic conditions

Org Lett. 2013 Mar 1;15(5):1092-5. doi: 10.1021/ol4001153. Epub 2013 Feb 18.

Abstract

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.