Practical N-Hydroxyphthalimide-Mediated Oxidation of Sulfonamides to N-Sulfonylimines

A new method to prepare sulfonylimines through the oxidation of sulfonamides mediated by N-hydroxyphthalimide under mild conditions has been developed. Compared to reported oxidation methods, broader substrates scope and milder conditions were achieved in our method. Importantly, this oxidation meth...

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Autores principales: Wang, Jian, Yi, Wen-Jing
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6832120/
https://www.ncbi.nlm.nih.gov/pubmed/31635092
http://dx.doi.org/10.3390/molecules24203771
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author Wang, Jian
Yi, Wen-Jing
author_facet Wang, Jian
Yi, Wen-Jing
author_sort Wang, Jian
collection PubMed
description A new method to prepare sulfonylimines through the oxidation of sulfonamides mediated by N-hydroxyphthalimide under mild conditions has been developed. Compared to reported oxidation methods, broader substrates scope and milder conditions were achieved in our method. Importantly, this oxidation method can afford N-sulfonyl enaminones using Mannich products as starting materials. Additionally, the one-pot Friedel–Crafts arylation reaction of unseparated N-sulfonylimine formed in our system with 1,3,5-trimethoxybenzene was successful without any additional catalyst.
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spelling pubmed-68321202019-11-20 Practical N-Hydroxyphthalimide-Mediated Oxidation of Sulfonamides to N-Sulfonylimines Wang, Jian Yi, Wen-Jing Molecules Article A new method to prepare sulfonylimines through the oxidation of sulfonamides mediated by N-hydroxyphthalimide under mild conditions has been developed. Compared to reported oxidation methods, broader substrates scope and milder conditions were achieved in our method. Importantly, this oxidation method can afford N-sulfonyl enaminones using Mannich products as starting materials. Additionally, the one-pot Friedel–Crafts arylation reaction of unseparated N-sulfonylimine formed in our system with 1,3,5-trimethoxybenzene was successful without any additional catalyst. MDPI 2019-10-19 /pmc/articles/PMC6832120/ /pubmed/31635092 http://dx.doi.org/10.3390/molecules24203771 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
Wang, Jian
Yi, Wen-Jing
Practical N-Hydroxyphthalimide-Mediated Oxidation of Sulfonamides to N-Sulfonylimines
title Practical N-Hydroxyphthalimide-Mediated Oxidation of Sulfonamides to N-Sulfonylimines
title_full Practical N-Hydroxyphthalimide-Mediated Oxidation of Sulfonamides to N-Sulfonylimines
title_fullStr Practical N-Hydroxyphthalimide-Mediated Oxidation of Sulfonamides to N-Sulfonylimines
title_full_unstemmed Practical N-Hydroxyphthalimide-Mediated Oxidation of Sulfonamides to N-Sulfonylimines
title_short Practical N-Hydroxyphthalimide-Mediated Oxidation of Sulfonamides to N-Sulfonylimines
title_sort practical n-hydroxyphthalimide-mediated oxidation of sulfonamides to n-sulfonylimines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6832120/
https://www.ncbi.nlm.nih.gov/pubmed/31635092
http://dx.doi.org/10.3390/molecules24203771
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