Intramolecular Oxidative Diaryl Coupling of Tetrasubstituted Diphenylamines for the Preparation of Bis(trifluoromethyl) Dimethyl Carbazoles

Abstract

Synthetic preparation of carbazoles can be challenging, requiring ring building strategies and/or precious metal catalysts. Presented herein is a method for preparation of carbazoles with the use of inexpensive and reliable hypervalent iodine chemistry. An oxidative single electron transfer (SET) event initiates cyclization for preparation of our trifluoromethyl carbazoles. This method has been shown to be useful for a variety of bis(trifluoromethyl)carbazole isomers that are of primary interest for use as battery materials.