Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate

[Image: see text] A method for the preparation of aryl and heteroaryl sulfonamides using 2,4,6-trichlorophenyl chlorosulfate (TCPC) is described. The reaction of 2-pyridylzinc reagents with TCPC resulted in 2,4,6-trichlorophenyl (TCP) pyridine-2-sulfonates, and the parent pyridine-2-sulfonate was sh...

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Autores principales: Colombe, James R., DeBergh, J. Robb, Buchwald, Stephen L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2015
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4477900/
https://www.ncbi.nlm.nih.gov/pubmed/26065317
http://dx.doi.org/10.1021/acs.orglett.5b01540
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author Colombe, James R.
DeBergh, J. Robb
Buchwald, Stephen L.
author_facet Colombe, James R.
DeBergh, J. Robb
Buchwald, Stephen L.
author_sort Colombe, James R.
collection PubMed
description [Image: see text] A method for the preparation of aryl and heteroaryl sulfonamides using 2,4,6-trichlorophenyl chlorosulfate (TCPC) is described. The reaction of 2-pyridylzinc reagents with TCPC resulted in 2,4,6-trichlorophenyl (TCP) pyridine-2-sulfonates, and the parent pyridine-2-sulfonate was shown to react with amines. Less electron-rich aryl- and heteroarylzinc reagents reacted with TCPC to afford sulfonyl chlorides that were converted in situ to sulfonamides.
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spelling pubmed-44779002016-06-11 Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate Colombe, James R. DeBergh, J. Robb Buchwald, Stephen L. Org Lett [Image: see text] A method for the preparation of aryl and heteroaryl sulfonamides using 2,4,6-trichlorophenyl chlorosulfate (TCPC) is described. The reaction of 2-pyridylzinc reagents with TCPC resulted in 2,4,6-trichlorophenyl (TCP) pyridine-2-sulfonates, and the parent pyridine-2-sulfonate was shown to react with amines. Less electron-rich aryl- and heteroarylzinc reagents reacted with TCPC to afford sulfonyl chlorides that were converted in situ to sulfonamides. American Chemical Society 2015-06-11 2015-06-19 /pmc/articles/PMC4477900/ /pubmed/26065317 http://dx.doi.org/10.1021/acs.orglett.5b01540 Text en Copyright © 2015 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Colombe, James R.
DeBergh, J. Robb
Buchwald, Stephen L.
Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate
title Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate
title_full Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate
title_fullStr Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate
title_full_unstemmed Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate
title_short Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate
title_sort synthesis of heteroaryl sulfonamides from organozinc reagents and 2,4,6-trichlorophenyl chlorosulfate
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4477900/
https://www.ncbi.nlm.nih.gov/pubmed/26065317
http://dx.doi.org/10.1021/acs.orglett.5b01540
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