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Cationic cobalt-catalyzed [1,3]-rearrangement of N-alkoxycarbonyloxyanilines

A cationic cobalt catalyst efficiently promoted the reaction of N-alkoxycarbonyloxyanilines at 30 °C, affording the corresponding ortho-aminophenols in good to high yields. As reported previously, our mechanistic studies including oxygen-18 labelling experiments indicate that the rearrangement of th...

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Autores principales: Nakamura, Itaru, Owada, Mao, Jo, Takeru, Terada, Masahiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6122159/
https://www.ncbi.nlm.nih.gov/pubmed/30202451
http://dx.doi.org/10.3762/bjoc.14.172
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author Nakamura, Itaru
Owada, Mao
Jo, Takeru
Terada, Masahiro
author_facet Nakamura, Itaru
Owada, Mao
Jo, Takeru
Terada, Masahiro
author_sort Nakamura, Itaru
collection PubMed
description A cationic cobalt catalyst efficiently promoted the reaction of N-alkoxycarbonyloxyanilines at 30 °C, affording the corresponding ortho-aminophenols in good to high yields. As reported previously, our mechanistic studies including oxygen-18 labelling experiments indicate that the rearrangement of the alkoxycarbonyloxy group proceeds in [1,3]-manner. In this article, we discuss the overall picture of the cobalt-catalysed [1,3]-rearrangement reaction including details of the reaction conditions and substrate scope.
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spelling pubmed-61221592018-09-10 Cationic cobalt-catalyzed [1,3]-rearrangement of N-alkoxycarbonyloxyanilines Nakamura, Itaru Owada, Mao Jo, Takeru Terada, Masahiro Beilstein J Org Chem Full Research Paper A cationic cobalt catalyst efficiently promoted the reaction of N-alkoxycarbonyloxyanilines at 30 °C, affording the corresponding ortho-aminophenols in good to high yields. As reported previously, our mechanistic studies including oxygen-18 labelling experiments indicate that the rearrangement of the alkoxycarbonyloxy group proceeds in [1,3]-manner. In this article, we discuss the overall picture of the cobalt-catalysed [1,3]-rearrangement reaction including details of the reaction conditions and substrate scope. Beilstein-Institut 2018-07-31 /pmc/articles/PMC6122159/ /pubmed/30202451 http://dx.doi.org/10.3762/bjoc.14.172 Text en Copyright © 2018, Nakamura 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 Full Research Paper
Nakamura, Itaru
Owada, Mao
Jo, Takeru
Terada, Masahiro
Cationic cobalt-catalyzed [1,3]-rearrangement of N-alkoxycarbonyloxyanilines
title Cationic cobalt-catalyzed [1,3]-rearrangement of N-alkoxycarbonyloxyanilines
title_full Cationic cobalt-catalyzed [1,3]-rearrangement of N-alkoxycarbonyloxyanilines
title_fullStr Cationic cobalt-catalyzed [1,3]-rearrangement of N-alkoxycarbonyloxyanilines
title_full_unstemmed Cationic cobalt-catalyzed [1,3]-rearrangement of N-alkoxycarbonyloxyanilines
title_short Cationic cobalt-catalyzed [1,3]-rearrangement of N-alkoxycarbonyloxyanilines
title_sort cationic cobalt-catalyzed [1,3]-rearrangement of n-alkoxycarbonyloxyanilines
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6122159/
https://www.ncbi.nlm.nih.gov/pubmed/30202451
http://dx.doi.org/10.3762/bjoc.14.172
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