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

Addison M. Duda; Michael T. Giurini; Jason G. Gillmore; Thomas F. Guarr

doi:10.1055/a-1662-7462

SynOpen, Inhaltsverzeichnis

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

Autoren

Addison M. Duda ∗

^aOrganic Energy Storage Laboratory, Michigan State University Bioeconomy Institute, 242 Howard Avenue, Holland, MI 49424, USA

^bDepartment of Chemistry, Duke University, 124 Science Drive, Durham, NC 27710, USA
Michael T. Giurini

^aOrganic Energy Storage Laboratory, Michigan State University Bioeconomy Institute, 242 Howard Avenue, Holland, MI 49424, USA
Jason G. Gillmore

^aOrganic Energy Storage Laboratory, Michigan State University Bioeconomy Institute, 242 Howard Avenue, Holland, MI 49424, USA

^cDepartment of Chemistry, Hope College, 35 East 12^th Street, Holland, MI 49423, USA
Thomas F. Guarr∗

^aOrganic Energy Storage Laboratory, Michigan State University Bioeconomy Institute, 242 Howard Avenue, Holland, MI 49424, USA

^dJolt Energy Storage Laboratory, 242 Howard Avenue, Holland, MI 49424, USA

Abstract

Alle Artikel dieser Rubrik

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

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Referenzen

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