Intermolecular addition reactions of N-alkyl-N-chlorosulfonamides to unsaturated compounds

N-Alkyl-N-chlorosulfonamides add to alkenes under copper(I) catalysis. In reactions of styrene derivatives with terminal double bonds the addition products were obtained in excellent yield and high regioselectivity. Lower yields are obtained in addition reactions to non-aromatic alkenes. The reactio...

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Autores principales: Heuger, Gerold, Göttlich, Richard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4578348/
https://www.ncbi.nlm.nih.gov/pubmed/26425180
http://dx.doi.org/10.3762/bjoc.11.136
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author Heuger, Gerold
Göttlich, Richard
author_facet Heuger, Gerold
Göttlich, Richard
author_sort Heuger, Gerold
collection PubMed
description N-Alkyl-N-chlorosulfonamides add to alkenes under copper(I) catalysis. In reactions of styrene derivatives with terminal double bonds the addition products were obtained in excellent yield and high regioselectivity. Lower yields are obtained in addition reactions to non-aromatic alkenes. The reaction most likely proceeds via a redox catalysis and amidyl radicals, a concerted mechanism has been ruled out and a polar mechanism via chloronium ions would lead to the opposite regiochemistry.
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spelling pubmed-45783482015-09-30 Intermolecular addition reactions of N-alkyl-N-chlorosulfonamides to unsaturated compounds Heuger, Gerold Göttlich, Richard Beilstein J Org Chem Full Research Paper N-Alkyl-N-chlorosulfonamides add to alkenes under copper(I) catalysis. In reactions of styrene derivatives with terminal double bonds the addition products were obtained in excellent yield and high regioselectivity. Lower yields are obtained in addition reactions to non-aromatic alkenes. The reaction most likely proceeds via a redox catalysis and amidyl radicals, a concerted mechanism has been ruled out and a polar mechanism via chloronium ions would lead to the opposite regiochemistry. Beilstein-Institut 2015-07-21 /pmc/articles/PMC4578348/ /pubmed/26425180 http://dx.doi.org/10.3762/bjoc.11.136 Text en Copyright © 2015, Heuger and Göttlich https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Heuger, Gerold
Göttlich, Richard
Intermolecular addition reactions of N-alkyl-N-chlorosulfonamides to unsaturated compounds
title Intermolecular addition reactions of N-alkyl-N-chlorosulfonamides to unsaturated compounds
title_full Intermolecular addition reactions of N-alkyl-N-chlorosulfonamides to unsaturated compounds
title_fullStr Intermolecular addition reactions of N-alkyl-N-chlorosulfonamides to unsaturated compounds
title_full_unstemmed Intermolecular addition reactions of N-alkyl-N-chlorosulfonamides to unsaturated compounds
title_short Intermolecular addition reactions of N-alkyl-N-chlorosulfonamides to unsaturated compounds
title_sort intermolecular addition reactions of n-alkyl-n-chlorosulfonamides to unsaturated compounds
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4578348/
https://www.ncbi.nlm.nih.gov/pubmed/26425180
http://dx.doi.org/10.3762/bjoc.11.136
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