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

Authors

• Addison M. Duda, Michigan State University
• Michael T. Giurini, Michigan State University
• Jason G. Gillmore, Michigan State University
• Thomas F. Guarr, Michigan State University

Document Type

Article

Publication Date

11-10-2021

Publication Source

Synopen

Volume Number

5

Issue Number

4

First Page

308

Last Page

313

E-ISSN

25099396

Abstract

Synthetic preparation of carbazoles can be challenging, requiring ring-building strategies and/or precious metal catalysts. Presented herein is a method for the preparation of carbazoles with the use of inexpensive and reliable hypervalent iodine chemistry. An oxidative single-electron-transfer (SET) event initiates cyclization for the 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.

Keywords

electron-deficient carbazoles, hypervalent iodine, intramolecular coupling, metal-free

Recommended Citation

Published in: Synopen, Volume 5, Issue 4, November 10, 2021, pages 308-313.