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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

© European Journal of Organic Chemistry, 2014, vol. 2014, p. 3188-3195

Wiley-VCH Verlag

Author: Güell Costa, Imma
Ribas Salamaña, Xavi
Date: 2014
Abstract: 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
ISSN: 1434-193X (versió paper)
1099-0690 (versió electrònica)
Document access: http://hdl.handle.net/10256/10205
Language: eng
Publisher: Wiley-VCH Verlag
Collection: MICINN/PN 2010-2016/CSD2010-00065
AGAUR/2009-2014/2009 SGR-637
MICINN/PN 2011/INP-2011-0059-PCT-420000
Reproducció digital del document publicat a: http://dx.doi.org/10.1002/ejoc.201400033
Articles publicats (D-Q)
info:eu-repo/grantAgreement/EC/FP7/277801
Is part of: © European Journal of Organic Chemistry, 2014, vol. 2014, p. 3188-3195
Rights: Tots els drets reservats
Subject: Coure
Copper
Sulfat de dimetil
Dimethyl sulfate
Catàlisi
Catalysis
Catalitzadors de coure
Copper catalysts
Title: Ligand-free Ullmann-type C-heteroatom couplings under practical conditions
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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