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

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...

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Autores principales:	Addison M. Duda, Michael T. Giurini, Jason G. Gillmore, Thomas F. Guarr
Formato:	article
Lenguaje:	EN
Publicado:	Georg Thieme Verlag KG 2021
Materias:	intramolecular coupling metal-free electron-deficient carbazoles hypervalent iodine Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/30fc6c0549524e72aeecbefe795f1a7b
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spelling	oai:doaj.org-article:30fc6c0549524e72aeecbefe795f1a7b2021-11-11T00:03:51ZIntramolecular Oxidative Diaryl Coupling of Tetrasubstituted Diphenylamines for the Preparation of Bis(trifluoromethyl) Dimethyl Carbazoles2509-939610.1055/a-1662-7462https://doaj.org/article/30fc6c0549524e72aeecbefe795f1a7b2021-10-01T00:00:00Zhttp://www.thieme-connect.de/DOI/DOI?10.1055/a-1662-7462https://doaj.org/toc/2509-9396Synthetic 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.Addison M. DudaMichael T. GiuriniJason G. GillmoreThomas F. GuarrGeorg Thieme Verlag KGarticleintramolecular couplingmetal-freeelectron-deficient carbazoleshypervalent iodineChemistryQD1-999ENSynOpen, Vol 05, Iss 04, Pp 308-313 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	intramolecular coupling metal-free electron-deficient carbazoles hypervalent iodine Chemistry QD1-999
spellingShingle	intramolecular coupling metal-free electron-deficient carbazoles hypervalent iodine Chemistry QD1-999 Addison M. Duda Michael T. Giurini Jason G. Gillmore Thomas F. Guarr Intramolecular Oxidative Diaryl Coupling of Tetrasubstituted Diphenylamines for the Preparation of Bis(trifluoromethyl) Dimethyl Carbazoles
description	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.
format	article
author	Addison M. Duda Michael T. Giurini Jason G. Gillmore Thomas F. Guarr
author_facet	Addison M. Duda Michael T. Giurini Jason G. Gillmore Thomas F. Guarr
author_sort	Addison M. Duda
title	Intramolecular Oxidative Diaryl Coupling of Tetrasubstituted Diphenylamines for the Preparation of Bis(trifluoromethyl) Dimethyl Carbazoles
title_short	Intramolecular Oxidative Diaryl Coupling of Tetrasubstituted Diphenylamines for the Preparation of Bis(trifluoromethyl) Dimethyl Carbazoles
title_full	Intramolecular Oxidative Diaryl Coupling of Tetrasubstituted Diphenylamines for the Preparation of Bis(trifluoromethyl) Dimethyl Carbazoles
title_fullStr	Intramolecular Oxidative Diaryl Coupling of Tetrasubstituted Diphenylamines for the Preparation of Bis(trifluoromethyl) Dimethyl Carbazoles
title_full_unstemmed	Intramolecular Oxidative Diaryl Coupling of Tetrasubstituted Diphenylamines for the Preparation of Bis(trifluoromethyl) Dimethyl Carbazoles
title_sort	intramolecular oxidative diaryl coupling of tetrasubstituted diphenylamines for the preparation of bis(trifluoromethyl) dimethyl carbazoles
publisher	Georg Thieme Verlag KG
publishDate	2021
url	https://doaj.org/article/30fc6c0549524e72aeecbefe795f1a7b
work_keys_str_mv	AT addisonmduda intramolecularoxidativediarylcouplingoftetrasubstituteddiphenylaminesforthepreparationofbistrifluoromethyldimethylcarbazoles AT michaeltgiurini intramolecularoxidativediarylcouplingoftetrasubstituteddiphenylaminesforthepreparationofbistrifluoromethyldimethylcarbazoles AT jasonggillmore intramolecularoxidativediarylcouplingoftetrasubstituteddiphenylaminesforthepreparationofbistrifluoromethyldimethylcarbazoles AT thomasfguarr intramolecularoxidativediarylcouplingoftetrasubstituteddiphenylaminesforthepreparationofbistrifluoromethyldimethylcarbazoles
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Intramolecular Oxidative Diaryl Coupling of Tetrasubstituted Diphenylamines for the Preparation of Bis(trifluoromethyl) Dimethyl Carbazoles

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