Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using o-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound

An oxidative 3-amination of indole derivatives using hypervalent iodine(III) and bissulfonimides, which proceeds via the formation of indolyl(aryl)iodonium imides, was developed. This reaction was followed by an indole-selective copper-catalyzed oxidative C–N coupling reaction to obtain 3-amino indo...

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Autores principales: Watanabe, Kazuhiro, Moriyama, Katsuhiko
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6471596/
https://www.ncbi.nlm.nih.gov/pubmed/30909483
http://dx.doi.org/10.3390/molecules24061147
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author Watanabe, Kazuhiro
Moriyama, Katsuhiko
author_facet Watanabe, Kazuhiro
Moriyama, Katsuhiko
author_sort Watanabe, Kazuhiro
collection PubMed
description An oxidative 3-amination of indole derivatives using hypervalent iodine(III) and bissulfonimides, which proceeds via the formation of indolyl(aryl)iodonium imides, was developed. This reaction was followed by an indole-selective copper-catalyzed oxidative C–N coupling reaction to obtain 3-amino indole derivatives as single regioisomers. o-Alkoxy(diacetoxyiodo)arenes showed higher reactivity in the reaction than o-alkyl(diacetoxyiodo)arenes, efficiently promoting the formation of indolyl(aryl)iodonium imides in the first step.
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spelling pubmed-64715962019-04-26 Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using o-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound Watanabe, Kazuhiro Moriyama, Katsuhiko Molecules Article An oxidative 3-amination of indole derivatives using hypervalent iodine(III) and bissulfonimides, which proceeds via the formation of indolyl(aryl)iodonium imides, was developed. This reaction was followed by an indole-selective copper-catalyzed oxidative C–N coupling reaction to obtain 3-amino indole derivatives as single regioisomers. o-Alkoxy(diacetoxyiodo)arenes showed higher reactivity in the reaction than o-alkyl(diacetoxyiodo)arenes, efficiently promoting the formation of indolyl(aryl)iodonium imides in the first step. MDPI 2019-03-22 /pmc/articles/PMC6471596/ /pubmed/30909483 http://dx.doi.org/10.3390/molecules24061147 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Watanabe, Kazuhiro
Moriyama, Katsuhiko
Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using o-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound
title Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using o-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound
title_full Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using o-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound
title_fullStr Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using o-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound
title_full_unstemmed Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using o-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound
title_short Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using o-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound
title_sort cu-catalyzed oxidative 3-amination of indoles via formation of indolyl(aryl)iodonium imides using o-substituted (diacetoxyiodo)arene as a high-performance hypervalent iodine compound
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6471596/
https://www.ncbi.nlm.nih.gov/pubmed/30909483
http://dx.doi.org/10.3390/molecules24061147
work_keys_str_mv AT watanabekazuhiro cucatalyzedoxidative3aminationofindolesviaformationofindolylaryliodoniumimidesusingosubstituteddiacetoxyiodoareneasahighperformancehypervalentiodinecompound
AT moriyamakatsuhiko cucatalyzedoxidative3aminationofindolesviaformationofindolylaryliodoniumimidesusingosubstituteddiacetoxyiodoareneasahighperformancehypervalentiodinecompound

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