Silver Catalyzed Site-Selective C(sp(3))−H Bond Amination of Secondary over Primary C(sp(3))−H Bonds

Sulfamates are widespread in numerous pharmacologically active molecules. In this paper, Silver/Bathophenanthroline catalyzed the intramolecular selective amination of primary C(sp(3))−H bonds and secondary C(sp(3))−H bonds of sulfamate esters, to produce cyclic sulfamates in good yields and with a...

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Detalles Bibliográficos
Autores principales: Jiao, Luzhen, Teng, Dawei, Wang, Zixuan, Cao, Guorui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9571442/
https://www.ncbi.nlm.nih.gov/pubmed/36234711
http://dx.doi.org/10.3390/molecules27196174
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author Jiao, Luzhen
Teng, Dawei
Wang, Zixuan
Cao, Guorui
author_facet Jiao, Luzhen
Teng, Dawei
Wang, Zixuan
Cao, Guorui
author_sort Jiao, Luzhen
collection PubMed
description Sulfamates are widespread in numerous pharmacologically active molecules. In this paper, Silver/Bathophenanthroline catalyzed the intramolecular selective amination of primary C(sp(3))−H bonds and secondary C(sp(3))−H bonds of sulfamate esters, to produce cyclic sulfamates in good yields and with a high site-selectivity. DFT calculations revealed that the interaction between sulfamates and L10 makes the molecule more firmly attached to the catalyst, benefiting the catalysis reaction. The in vitro anticancer activity of the final products was evaluated in MCF-7 breast cancer cells.
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spelling pubmed-95714422022-10-17 Silver Catalyzed Site-Selective C(sp(3))−H Bond Amination of Secondary over Primary C(sp(3))−H Bonds Jiao, Luzhen Teng, Dawei Wang, Zixuan Cao, Guorui Molecules Article Sulfamates are widespread in numerous pharmacologically active molecules. In this paper, Silver/Bathophenanthroline catalyzed the intramolecular selective amination of primary C(sp(3))−H bonds and secondary C(sp(3))−H bonds of sulfamate esters, to produce cyclic sulfamates in good yields and with a high site-selectivity. DFT calculations revealed that the interaction between sulfamates and L10 makes the molecule more firmly attached to the catalyst, benefiting the catalysis reaction. The in vitro anticancer activity of the final products was evaluated in MCF-7 breast cancer cells. MDPI 2022-09-21 /pmc/articles/PMC9571442/ /pubmed/36234711 http://dx.doi.org/10.3390/molecules27196174 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Jiao, Luzhen
Teng, Dawei
Wang, Zixuan
Cao, Guorui
Silver Catalyzed Site-Selective C(sp(3))−H Bond Amination of Secondary over Primary C(sp(3))−H Bonds
title Silver Catalyzed Site-Selective C(sp(3))−H Bond Amination of Secondary over Primary C(sp(3))−H Bonds
title_full Silver Catalyzed Site-Selective C(sp(3))−H Bond Amination of Secondary over Primary C(sp(3))−H Bonds
title_fullStr Silver Catalyzed Site-Selective C(sp(3))−H Bond Amination of Secondary over Primary C(sp(3))−H Bonds
title_full_unstemmed Silver Catalyzed Site-Selective C(sp(3))−H Bond Amination of Secondary over Primary C(sp(3))−H Bonds
title_short Silver Catalyzed Site-Selective C(sp(3))−H Bond Amination of Secondary over Primary C(sp(3))−H Bonds
title_sort silver catalyzed site-selective c(sp(3))−h bond amination of secondary over primary c(sp(3))−h bonds
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9571442/
https://www.ncbi.nlm.nih.gov/pubmed/36234711
http://dx.doi.org/10.3390/molecules27196174
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AT wangzixuan silvercatalyzedsiteselectivecsp3hbondaminationofsecondaryoverprimarycsp3hbonds
AT caoguorui silvercatalyzedsiteselectivecsp3hbondaminationofsecondaryoverprimarycsp3hbonds

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