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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-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

The 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 award

Wiley-VCH Verlag

Director: Ministerio de Ciencia e Innovación (Espanya)
Generalitat de Catalunya. Agència de Gestió d’Ajuts Universitaris i de Recerca
Autor: Güell Costa, Imma
Ribas Salamaña, Xavi
Data: 2014
Resum: 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
The 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 award
Format: application/pdf
Accés al document: http://hdl.handle.net/10256/10205
Llenguatge: eng
Editor: Wiley-VCH Verlag
Col·lecció: 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/EU/Sustainable C-X and C-H Functionalization Catalyzed by Copper(III) Species/SUSCATCU3
Drets: Tots els drets reservats
Matèria: Coure
Copper
Sulfat de dimetil
Dimethyl sulfate
Catàlisi
Catalysis
Catalitzadors de coure
Copper catalysts
Títol: Ligand-free Ullmann-type C-heteroatom couplings under practical conditions
Tipus: info:eu-repo/semantics/article
Repositori: DUGiDocs

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