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CC BY-NC-ND 4.0 · SynOpen 2021; 05(04): 308-313
DOI: 10.1055/a-1662-7462
paper

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

Addison M. Duda  ∗
a   Organic Energy Storage Laboratory, Michigan State University Bioeconomy Institute, 242 Howard Avenue, Holland, MI 49424, USA
b   Department of Chemistry, Duke University, 124 Science Drive, Durham, NC 27710, USA
,
Michael T. Giurini 
a   Organic Energy Storage Laboratory, Michigan State University Bioeconomy Institute, 242 Howard Avenue, Holland, MI 49424, USA
,
Jason G. Gillmore 
a   Organic Energy Storage Laboratory, Michigan State University Bioeconomy Institute, 242 Howard Avenue, Holland, MI 49424, USA
c   Department of Chemistry, Hope College, 35 East 12th Street, Holland, MI 49423, USA
,
Thomas F. Guarr∗
a   Organic Energy Storage Laboratory, Michigan State University Bioeconomy Institute, 242 Howard Avenue, Holland, MI 49424, USA
d   Jolt Energy Storage Laboratory, 242 Howard Avenue, Holland, MI 49424, USA
› Author AffiliationsFunding support provided by the Community Foundation of the Holland­/Zeeland area of Michigan and the Michigan Strategic Fund with Lakeshore Advantage. Agilent 6224 LC/MS-TOF (High Resolution) was supported by the National Science Foundation (NSF) (Grant Number CHE-0923097).
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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.

Key words

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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1662-7462.
  • Supporting Information


Publication History

Received: 01 September 2021

Accepted after revision: 05 October 2021

Accepted Manuscript online:
06 October 2021

Article published online:
10 November 2021

© 2021. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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