Are Cu(I)-mesoionic NHC carbenes associated with nitrogen additives the best Cu-carbene catalysts for the azide-alkyne click reaction in solution? A case study. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Tetrahedron Letters Année : 2013

Are Cu(I)-mesoionic NHC carbenes associated with nitrogen additives the best Cu-carbene catalysts for the azide-alkyne click reaction in solution? A case study.

Stephan Hohloch
  • Fonction : Auteur
Biprajit Sarkar
  • Fonction : Auteur
Lionel Nauton
Federico Cisnetti

Résumé

Copper(I)-catalyzed azide alkyne cycloaddition is now a widely used tool for the synthesis of elaborated compounds. Until now, few stable and efficient copper(I) catalysts are available despite the limitations inherent to approaches employing the in situ reduction of a CuII species to deliver the catalytic system. We report that the combination of a copper(I)-mesoionic N-heterocyclic carbene (MIC) with a phenanthroline derivative generates a highly active catalyst, functioning in aqueous alcoholic solvent, without the intervention of a reducing agent. This catalytic system surpasses related 'normal' N-heterocyclic carbene-based systems in their efficiency.
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Dates et versions

hal-00812528 , version 1 (12-04-2013)

Identifiants

  • HAL Id : hal-00812528 , version 1

Citer

Stephan Hohloch, Biprajit Sarkar, Lionel Nauton, Federico Cisnetti, Arnaud Gautier. Are Cu(I)-mesoionic NHC carbenes associated with nitrogen additives the best Cu-carbene catalysts for the azide-alkyne click reaction in solution? A case study.. Tetrahedron Letters, 2013, 54, pp.1808-1812. ⟨hal-00812528⟩
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