Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent

The trifluoromethylation of iodoarenes was accomplished by use of a 2-trifluoromethylbenzimidazoline derivative as the trifluoromethylating reagent and a catalytic amount of Cu(I) in the presence of 2,2'-bipyridyl as the ligand. Through a mechanistic study, we found that the oxidative addition...

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Autores principales: Uchikura, Tatsuhiro, Kamiyama, Nanami, Ishikawa, Taisuke, Akiyama, Takahiko
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7537379/
https://www.ncbi.nlm.nih.gov/pubmed/33082878
http://dx.doi.org/10.3762/bjoc.16.198
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author Uchikura, Tatsuhiro
Kamiyama, Nanami
Ishikawa, Taisuke
Akiyama, Takahiko
author_facet Uchikura, Tatsuhiro
Kamiyama, Nanami
Ishikawa, Taisuke
Akiyama, Takahiko
author_sort Uchikura, Tatsuhiro
collection PubMed
description The trifluoromethylation of iodoarenes was accomplished by use of a 2-trifluoromethylbenzimidazoline derivative as the trifluoromethylating reagent and a catalytic amount of Cu(I) in the presence of 2,2'-bipyridyl as the ligand. Through a mechanistic study, we found that the oxidative addition of the iodoarene to the Cu(I)–CF(3) species is the rate-determining step.
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spelling pubmed-75373792020-10-19 Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent Uchikura, Tatsuhiro Kamiyama, Nanami Ishikawa, Taisuke Akiyama, Takahiko Beilstein J Org Chem Letter The trifluoromethylation of iodoarenes was accomplished by use of a 2-trifluoromethylbenzimidazoline derivative as the trifluoromethylating reagent and a catalytic amount of Cu(I) in the presence of 2,2'-bipyridyl as the ligand. Through a mechanistic study, we found that the oxidative addition of the iodoarene to the Cu(I)–CF(3) species is the rate-determining step. Beilstein-Institut 2020-09-30 /pmc/articles/PMC7537379/ /pubmed/33082878 http://dx.doi.org/10.3762/bjoc.16.198 Text en Copyright © 2020, Uchikura et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Uchikura, Tatsuhiro
Kamiyama, Nanami
Ishikawa, Taisuke
Akiyama, Takahiko
Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent
title Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent
title_full Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent
title_fullStr Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent
title_full_unstemmed Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent
title_short Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent
title_sort catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7537379/
https://www.ncbi.nlm.nih.gov/pubmed/33082878
http://dx.doi.org/10.3762/bjoc.16.198
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