Ligand-free Ullmann-type C-heteroatom couplings under practical conditions

A new practical ligand-free protocol for copper-catalyzed C-heteroatom cross-coupling reactions (Ullmann-type) is described. The use of dimethyl sulfoxide (DMSO) as the solvent overcomes the need to use organic auxiliary ligands; thus, DMSO is revealed as a nontoxic and superior solvent for Ullmann-...

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Detalhes bibliográficos
Autores: Güell Costa, Imma, Ribas Salamaña, Xavi
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2014
País:España
Recursos: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:10256/10205
Acesso em linha:http://hdl.handle.net/10256/10205
Access Level:acceso embargado
Palavra-chave:Coure
Copper
Sulfat de dimetil
Dimethyl sulfate
Catàlisi
Catalysis
Catalitzadors de coure
Copper catalysts
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spelling Ligand-free Ullmann-type C-heteroatom couplings under practical conditionsGüell Costa, ImmaRibas Salamaña, XaviCoureCopperSulfat de dimetilDimethyl sulfateCatàlisiCatalysisCatalitzadors de coureCopper catalystsA new practical ligand-free protocol for copper-catalyzed C-heteroatom cross-coupling reactions (Ullmann-type) is described. The use of dimethyl sulfoxide (DMSO) as the solvent overcomes the need to use organic auxiliary ligands; thus, DMSO is revealed as a nontoxic and superior solvent for Ullmann-type coupling reactions. This method allows the arylation of a wide range of amides, alcohols, and amines under practical conditions with bromobenzene and iodobenzene derivatives and will likely find direct application in current organic synthesis. The competitive reactivity among different functional groups is reported and rationalized, and the possibility to achieve selective arylation reactions is demonstratedThe authors acknowledge financial support from the European Research Council for Starting Grant Project (ERC-2011-StG-277801), from the Spanish Ministerio de Economia y Competitividad (Consolider-Ingenio CSD2010-00065, INNPLANTA project INP-2011-0059-PCT-420000-ACT1) and from the Generalitat de Catalunya (2009SGR637). X. R. also thanks the Institucio Catalana de Recerca i Estudis Avancats (ICREA) for an ICREA-Academia awardWiley-VCH VerlagMinisterio de Ciencia e Innovación (Espanya)Generalitat de Catalunya. Agència de Gestió d'Ajuts Universitaris i de Recercainfoinfo2014info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/10256/10205http://hdl.handle.net/10256/10205© European Journal of Organic Chemistry, 2014, vol. 2014, p. 3188-3195Articles 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/ejoc.201400033info:eu-repo/semantics/altIdentifier/issn/1434-193Xinfo:eu-repo/semantics/altIdentifier/eissn/1099-0690MICINN/PN 2010-2016/CSD2010-00065AGAUR/2009-2014/2009 SGR-637MICINN/PN 2011/INP-2011-0059-PCT-420000info:eu-repo/grantAgreement/EC/FP7/277801Tots els drets reservatsinfo:eu-repo/semantics/embargoedAccessoai:recercat.cat:10256/102052026-05-29T05:05:01Z
dc.title.none.fl_str_mv Ligand-free Ullmann-type C-heteroatom couplings under practical conditions
title Ligand-free Ullmann-type C-heteroatom couplings under practical conditions
spellingShingle Ligand-free Ullmann-type C-heteroatom couplings under practical conditions
Güell Costa, Imma
Coure
Copper
Sulfat de dimetil
Dimethyl sulfate
Catàlisi
Catalysis
Catalitzadors de coure
Copper catalysts
title_short Ligand-free Ullmann-type C-heteroatom couplings under practical conditions
title_full Ligand-free Ullmann-type C-heteroatom couplings under practical conditions
title_fullStr Ligand-free Ullmann-type C-heteroatom couplings under practical conditions
title_full_unstemmed Ligand-free Ullmann-type C-heteroatom couplings under practical conditions
title_sort Ligand-free Ullmann-type C-heteroatom couplings under practical conditions
dc.creator.none.fl_str_mv Güell Costa, Imma
Ribas Salamaña, Xavi
author Güell Costa, Imma
author_facet Güell Costa, Imma
Ribas Salamaña, Xavi
author_role author
author2 Ribas Salamaña, Xavi
author2_role author
dc.contributor.none.fl_str_mv Ministerio de Ciencia e Innovación (Espanya)
Generalitat de Catalunya. Agència de Gestió d'Ajuts Universitaris i de Recerca
dc.subject.none.fl_str_mv Coure
Copper
Sulfat de dimetil
Dimethyl sulfate
Catàlisi
Catalysis
Catalitzadors de coure
Copper catalysts
topic Coure
Copper
Sulfat de dimetil
Dimethyl sulfate
Catàlisi
Catalysis
Catalitzadors de coure
Copper catalysts
description A new practical ligand-free protocol for copper-catalyzed C-heteroatom cross-coupling reactions (Ullmann-type) is described. The use of dimethyl sulfoxide (DMSO) as the solvent overcomes the need to use organic auxiliary ligands; thus, DMSO is revealed as a nontoxic and superior solvent for Ullmann-type coupling reactions. This method allows the arylation of a wide range of amides, alcohols, and amines under practical conditions with bromobenzene and iodobenzene derivatives and will likely find direct application in current organic synthesis. The competitive reactivity among different functional groups is reported and rationalized, and the possibility to achieve selective arylation reactions is demonstrated
publishDate 2014
dc.date.none.fl_str_mv 2014
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/10256/10205
http://hdl.handle.net/10256/10205
url http://hdl.handle.net/10256/10205
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/ejoc.201400033
info:eu-repo/semantics/altIdentifier/issn/1434-193X
info:eu-repo/semantics/altIdentifier/eissn/1099-0690
MICINN/PN 2010-2016/CSD2010-00065
AGAUR/2009-2014/2009 SGR-637
MICINN/PN 2011/INP-2011-0059-PCT-420000
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-VCH Verlag
publisher.none.fl_str_mv Wiley-VCH Verlag
dc.source.none.fl_str_mv © European Journal of Organic Chemistry, 2014, vol. 2014, p. 3188-3195
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 15.198674

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