Published January 1, 2015 | Version v1
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Copper-Catalysed Allylic Substitution Using 2,8,14,20-Tetrapentylresorcinarenyl-Substituted Imidazolium Salts

  • 1. Univ Strasbourg, Lab Chim Inorgan & Catalyse, UMR CNRS 7177, F-67070 Strasbourg, France
  • 2. Inonu Univ, Dept Chem, Fac Sci & Art, TR-44280 Malatya, Turkey
  • 3. Cumhuriyet Univ, Dept Chem, Fac Sci, TR-58140 Sivas, Turkey
  • 4. Univ Rennes 1, Inst Phys, UMR CNRS 6251, F-35042 Rennes, France

Description

Unsymmetrical imidazolium salts, each having one nitrogen atom (N1) substituted by a cavity-shaped TPR group (TPR = 2,8,14,20-tetrapentylresorcinaren-5-yl), were tested in situ as proligands for the copper-catalysed allylic arylation of cinnamyl bromide with arylmagnesium halides. The catalytic systems produced mixtures of linear (l) and branched (b) arylated compounds in variable proportions, with the b/l ratio being the highest (78:22) for the most crowded imidazolium salt used, namely that in which the second nitrogen atom (N2) was substituted by a mesityl group. An N-heterocyclic carbene complex obtained from one of the imidazolium salts was characterised by an X-ray diffraction study.

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