Sulfonylation of 1,4‐Diazabicyclo[2.2.2]octane: Charge‐Transfer Complex Triggered C−N Bond Cleavage

A novel charge‐transfer complex triggered sulfonylation of 1,4‐diazabicyclo[2.2.2]octane (DABCO) with mild reaction conditions has been developed. The formation of a charge‐transfer complex between electron‐withdrawing (hetero)aryl sulfonyl chloride and DABCO allows the synthesis of N‐ethylated pipe...

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Detalles Bibliográficos
Autores principales: Fu, Ying, Xu, Qin‐Shan, Li, Quan‐Zhou, Li, Ming‐Peng, Shi, Chun‐Zhao, Du, Zhengyin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6350051/
https://www.ncbi.nlm.nih.gov/pubmed/30723657
http://dx.doi.org/10.1002/open.201800251
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author Fu, Ying
Xu, Qin‐Shan
Li, Quan‐Zhou
Li, Ming‐Peng
Shi, Chun‐Zhao
Du, Zhengyin
author_facet Fu, Ying
Xu, Qin‐Shan
Li, Quan‐Zhou
Li, Ming‐Peng
Shi, Chun‐Zhao
Du, Zhengyin
author_sort Fu, Ying
collection PubMed
description A novel charge‐transfer complex triggered sulfonylation of 1,4‐diazabicyclo[2.2.2]octane (DABCO) with mild reaction conditions has been developed. The formation of a charge‐transfer complex between electron‐withdrawing (hetero)aryl sulfonyl chloride and DABCO allows the synthesis of N‐ethylated piperazine sulfonamide in good yields. The reaction has a high functional group tolerance. Spectroscopic studies confirmed the charge‐transfer complex formation between sulfonyl chlorides and DABCO, which facilitates the C−N bond cleavage of DABCO.
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spelling pubmed-63500512019-02-05 Sulfonylation of 1,4‐Diazabicyclo[2.2.2]octane: Charge‐Transfer Complex Triggered C−N Bond Cleavage Fu, Ying Xu, Qin‐Shan Li, Quan‐Zhou Li, Ming‐Peng Shi, Chun‐Zhao Du, Zhengyin ChemistryOpen Communications A novel charge‐transfer complex triggered sulfonylation of 1,4‐diazabicyclo[2.2.2]octane (DABCO) with mild reaction conditions has been developed. The formation of a charge‐transfer complex between electron‐withdrawing (hetero)aryl sulfonyl chloride and DABCO allows the synthesis of N‐ethylated piperazine sulfonamide in good yields. The reaction has a high functional group tolerance. Spectroscopic studies confirmed the charge‐transfer complex formation between sulfonyl chlorides and DABCO, which facilitates the C−N bond cleavage of DABCO. John Wiley and Sons Inc. 2019-01-28 /pmc/articles/PMC6350051/ /pubmed/30723657 http://dx.doi.org/10.1002/open.201800251 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Fu, Ying
Xu, Qin‐Shan
Li, Quan‐Zhou
Li, Ming‐Peng
Shi, Chun‐Zhao
Du, Zhengyin
Sulfonylation of 1,4‐Diazabicyclo[2.2.2]octane: Charge‐Transfer Complex Triggered C−N Bond Cleavage
title Sulfonylation of 1,4‐Diazabicyclo[2.2.2]octane: Charge‐Transfer Complex Triggered C−N Bond Cleavage
title_full Sulfonylation of 1,4‐Diazabicyclo[2.2.2]octane: Charge‐Transfer Complex Triggered C−N Bond Cleavage
title_fullStr Sulfonylation of 1,4‐Diazabicyclo[2.2.2]octane: Charge‐Transfer Complex Triggered C−N Bond Cleavage
title_full_unstemmed Sulfonylation of 1,4‐Diazabicyclo[2.2.2]octane: Charge‐Transfer Complex Triggered C−N Bond Cleavage
title_short Sulfonylation of 1,4‐Diazabicyclo[2.2.2]octane: Charge‐Transfer Complex Triggered C−N Bond Cleavage
title_sort sulfonylation of 1,4‐diazabicyclo[2.2.2]octane: charge‐transfer complex triggered c−n bond cleavage
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6350051/
https://www.ncbi.nlm.nih.gov/pubmed/30723657
http://dx.doi.org/10.1002/open.201800251
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