Intramolecular 1,5-C(sp(3))–H radical amination via Co(ii)-based metalloradical catalysis for five-membered cyclic sulfamides

Co(ii)-based metalloradical catalysis (MRC) proves effective for intramolecular 1,5-C–H amination of sulfamoyl azides under neutral and nonoxidative conditions, providing a straightforward approach to access strained 5-membered cyclic sulfamides with nitrogen gas as the only byproduct. The metallora...

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Autores principales: Lu, Hongjian, Lang, Kai, Jiang, Huiling, Wojtas, Lukasz, Zhang, X. Peter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5271564/
https://www.ncbi.nlm.nih.gov/pubmed/28138382
http://dx.doi.org/10.1039/c6sc02231f
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author Lu, Hongjian
Lang, Kai
Jiang, Huiling
Wojtas, Lukasz
Zhang, X. Peter
author_facet Lu, Hongjian
Lang, Kai
Jiang, Huiling
Wojtas, Lukasz
Zhang, X. Peter
author_sort Lu, Hongjian
collection PubMed
description Co(ii)-based metalloradical catalysis (MRC) proves effective for intramolecular 1,5-C–H amination of sulfamoyl azides under neutral and nonoxidative conditions, providing a straightforward approach to access strained 5-membered cyclic sulfamides with nitrogen gas as the only byproduct. The metalloradical amination system is applicable to different types of C(sp(3))–H bonds and has a high degree of functional group tolerance. Additional features of the Co(ii)-catalyzed 1,5-C–H amination include excellent chemoselectivity toward allylic and propargylic C–H bonds. The unique reactivity and selectivity profile of the Co(ii)-catalyzed 1,5-C–H amination is attributed to the underlying radical mechanism of MRC.
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spelling pubmed-52715642017-07-28 Intramolecular 1,5-C(sp(3))–H radical amination via Co(ii)-based metalloradical catalysis for five-membered cyclic sulfamides Lu, Hongjian Lang, Kai Jiang, Huiling Wojtas, Lukasz Zhang, X. Peter Chem Sci Chemistry Co(ii)-based metalloradical catalysis (MRC) proves effective for intramolecular 1,5-C–H amination of sulfamoyl azides under neutral and nonoxidative conditions, providing a straightforward approach to access strained 5-membered cyclic sulfamides with nitrogen gas as the only byproduct. The metalloradical amination system is applicable to different types of C(sp(3))–H bonds and has a high degree of functional group tolerance. Additional features of the Co(ii)-catalyzed 1,5-C–H amination include excellent chemoselectivity toward allylic and propargylic C–H bonds. The unique reactivity and selectivity profile of the Co(ii)-catalyzed 1,5-C–H amination is attributed to the underlying radical mechanism of MRC. Royal Society of Chemistry 2016-12-01 2016-07-28 /pmc/articles/PMC5271564/ /pubmed/28138382 http://dx.doi.org/10.1039/c6sc02231f Text en This journal is © The Royal Society of Chemistry 2016 https://creativecommons.org/licenses/by/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Lu, Hongjian
Lang, Kai
Jiang, Huiling
Wojtas, Lukasz
Zhang, X. Peter
Intramolecular 1,5-C(sp(3))–H radical amination via Co(ii)-based metalloradical catalysis for five-membered cyclic sulfamides
title Intramolecular 1,5-C(sp(3))–H radical amination via Co(ii)-based metalloradical catalysis for five-membered cyclic sulfamides
title_full Intramolecular 1,5-C(sp(3))–H radical amination via Co(ii)-based metalloradical catalysis for five-membered cyclic sulfamides
title_fullStr Intramolecular 1,5-C(sp(3))–H radical amination via Co(ii)-based metalloradical catalysis for five-membered cyclic sulfamides
title_full_unstemmed Intramolecular 1,5-C(sp(3))–H radical amination via Co(ii)-based metalloradical catalysis for five-membered cyclic sulfamides
title_short Intramolecular 1,5-C(sp(3))–H radical amination via Co(ii)-based metalloradical catalysis for five-membered cyclic sulfamides
title_sort intramolecular 1,5-c(sp(3))–h radical amination via co(ii)-based metalloradical catalysis for five-membered cyclic sulfamides
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5271564/
https://www.ncbi.nlm.nih.gov/pubmed/28138382
http://dx.doi.org/10.1039/c6sc02231f
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