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Article Dans Une Revue ChemCatChem Année : 2013

Palladium-Catalysed Direct Polyarylation of Pyrrole Derivatives

Liqin Zhao
  • Fonction : Auteur
Henri Doucet
  • Fonction : Auteur
  • PersonId : 853725

Résumé

The palladium-catalysed direct polyarylation of 1-methylpyrrole and 1-phenylpyrrole was studied. As the C2 and C5 positions of pyrroles are more reactive for C-H bond functionalisation than the C3 and C4 positions, the formation of 2,5-diarylpyrroles was found to proceed selectively in the presence of 3 equiv. of a variety of aryl bromides. The sequential C2 arylation followed by C5 arylation to prepare non-symmetrically substituted 2,5-diarylpyrroles was also studied. For the synthesis of such pyrroles, higher yields were obtained for the couplings with electron-deficient aryl bromides. The tetraarylation of 1-methylpyrrole was also achieved. From 4 equiv. of 3,5-bis(trifluoromethyl) bromobenzene, the 2,3,4,5-tetraarylated pyrrole was obtained in good yield.

Domaines

Chimie organique

Dates et versions

hal-00811421 , version 1 (10-04-2013)

Identifiants

Citer

Liqin Zhao, Christian Bruneau, Henri Doucet. Palladium-Catalysed Direct Polyarylation of Pyrrole Derivatives. ChemCatChem, 2013, 5 (1), pp.255-262. ⟨10.1002/cctc.201200521⟩. ⟨hal-00811421⟩
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