Regioselective Access to Sultam Motifs through Cobalt-Catalyzed Annulation of Aryl Sulfonamides and Alkynes using an 8-Aminoquinoline Directing Group

The use of cobalt as catalyst in direct C-H activation protocols as a replacement for more expensive second row transition metals is currently attracting significant attention. Herein we disclose a facile cobalt-catalyzed C-H functionalization route towards sultam motifs through annulation of easily...

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Autores: Planas Fàbrega, Oriol, Whiteoak, Christopher J., Company Casadevall, Anna, Ribas Salamaña, Xavi
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2015
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10256/12495
Acceso en línea:http://hdl.handle.net/10256/12495
Access Level:acceso embargado
Palabra clave:Alquins
Alkynes
Activació (Química)
Activation (Chemistry)
Reaccions químiques regioselectives
Chemical reactions
Sulfonamides
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spelling Regioselective Access to Sultam Motifs through Cobalt-Catalyzed Annulation of Aryl Sulfonamides and Alkynes using an 8-Aminoquinoline Directing GroupPlanas Fàbrega, OriolWhiteoak, Christopher J.Company Casadevall, AnnaRibas Salamaña, XaviAlquinsAlkynesActivació (Química)Activation (Chemistry)Reaccions químiques regioselectivesChemical reactionsSulfonamidesSulfonamidesThe use of cobalt as catalyst in direct C-H activation protocols as a replacement for more expensive second row transition metals is currently attracting significant attention. Herein we disclose a facile cobalt-catalyzed C-H functionalization route towards sultam motifs through annulation of easily prepared aryl sulfonamides and alkynes using 8-aminoquinoline as a directing group. The reaction shows broad substrate scope with products obtained in a highly regioselective manner in good to excellent isolated yields. Mechanistic insights suggest the formation of a Co(III)-aryl key species via a rate-determining arene C-H activation during the annulation reactionWe acknowledge financial support from the ERC for the Starting Grant Project ERC-2011-StG-277801 to X.R. and MINECO of Spain for CTQ2013-43012-P to X.R. and A.C, and a RyC contract to A.C.WileyMinisterio de Economía y Competitividad (Espanya)infoinfo2015info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/10256/12495http://hdl.handle.net/10256/12495© Advanced Synthesis and Catalysis, 2015, vol. 357, núm. 18, p. 4003-4012Articles publicats (D-Q)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1002/adsc.201500690info:eu-repo/semantics/altIdentifier/issn/1615-4150info:eu-repo/semantics/altIdentifier/eissn/1615-4169info:eu-repo/grantAgreement/MINECO//CTQ2013-43012-Pinfo:eu-repo/grantAgreement/EC/FP7/277801Tots els drets reservatsinfo:eu-repo/semantics/embargoedAccessoai:recercat.cat:10256/124952026-05-29T05:05:01Z
dc.title.none.fl_str_mv Regioselective Access to Sultam Motifs through Cobalt-Catalyzed Annulation of Aryl Sulfonamides and Alkynes using an 8-Aminoquinoline Directing Group
title Regioselective Access to Sultam Motifs through Cobalt-Catalyzed Annulation of Aryl Sulfonamides and Alkynes using an 8-Aminoquinoline Directing Group
spellingShingle Regioselective Access to Sultam Motifs through Cobalt-Catalyzed Annulation of Aryl Sulfonamides and Alkynes using an 8-Aminoquinoline Directing Group
Planas Fàbrega, Oriol
Alquins
Alkynes
Activació (Química)
Activation (Chemistry)
Reaccions químiques regioselectives
Chemical reactions
Sulfonamides
Sulfonamides
title_short Regioselective Access to Sultam Motifs through Cobalt-Catalyzed Annulation of Aryl Sulfonamides and Alkynes using an 8-Aminoquinoline Directing Group
title_full Regioselective Access to Sultam Motifs through Cobalt-Catalyzed Annulation of Aryl Sulfonamides and Alkynes using an 8-Aminoquinoline Directing Group
title_fullStr Regioselective Access to Sultam Motifs through Cobalt-Catalyzed Annulation of Aryl Sulfonamides and Alkynes using an 8-Aminoquinoline Directing Group
title_full_unstemmed Regioselective Access to Sultam Motifs through Cobalt-Catalyzed Annulation of Aryl Sulfonamides and Alkynes using an 8-Aminoquinoline Directing Group
title_sort Regioselective Access to Sultam Motifs through Cobalt-Catalyzed Annulation of Aryl Sulfonamides and Alkynes using an 8-Aminoquinoline Directing Group
dc.creator.none.fl_str_mv Planas Fàbrega, Oriol
Whiteoak, Christopher J.
Company Casadevall, Anna
Ribas Salamaña, Xavi
author Planas Fàbrega, Oriol
author_facet Planas Fàbrega, Oriol
Whiteoak, Christopher J.
Company Casadevall, Anna
Ribas Salamaña, Xavi
author_role author
author2 Whiteoak, Christopher J.
Company Casadevall, Anna
Ribas Salamaña, Xavi
author2_role author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (Espanya)
dc.subject.none.fl_str_mv Alquins
Alkynes
Activació (Química)
Activation (Chemistry)
Reaccions químiques regioselectives
Chemical reactions
Sulfonamides
Sulfonamides
topic Alquins
Alkynes
Activació (Química)
Activation (Chemistry)
Reaccions químiques regioselectives
Chemical reactions
Sulfonamides
Sulfonamides
description The use of cobalt as catalyst in direct C-H activation protocols as a replacement for more expensive second row transition metals is currently attracting significant attention. Herein we disclose a facile cobalt-catalyzed C-H functionalization route towards sultam motifs through annulation of easily prepared aryl sulfonamides and alkynes using 8-aminoquinoline as a directing group. The reaction shows broad substrate scope with products obtained in a highly regioselective manner in good to excellent isolated yields. Mechanistic insights suggest the formation of a Co(III)-aryl key species via a rate-determining arene C-H activation during the annulation reaction
publishDate 2015
dc.date.none.fl_str_mv 2015
info
info
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10256/12495
http://hdl.handle.net/10256/12495
url http://hdl.handle.net/10256/12495
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/adsc.201500690
info:eu-repo/semantics/altIdentifier/issn/1615-4150
info:eu-repo/semantics/altIdentifier/eissn/1615-4169
info:eu-repo/grantAgreement/MINECO//CTQ2013-43012-P
info:eu-repo/grantAgreement/EC/FP7/277801
dc.rights.none.fl_str_mv Tots els drets reservats
info:eu-repo/semantics/embargoedAccess
rights_invalid_str_mv Tots els drets reservats
eu_rights_str_mv embargoedAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv © Advanced Synthesis and Catalysis, 2015, vol. 357, núm. 18, p. 4003-4012
Articles publicats (D-Q)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,811543

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