Metal-Free Intra- and Intermolecular Oxidative C-N Bond Formation

Significance

Following the report of Chang and co-workers on metal-free intramolecular oxidative C-N bond formation for the synthesis of carbazoles (J. Am. Chem. Soc. 2011, 133, 5996), the authors report the first organocatalytic version of this reaction using a hypervalent iodine catalyst prepared in situ from a catalytic amount of a iodo(I)arene and peracetic acid. The authors also describe the intermolecular cross-amination reactions of anilines. These are the first examples of intermolecular C-H amination of unactivated ar­enes. Unfortunately, attempts to carry out the catalytic version of this intermolecular transformation has been unsuccessful.