Copper-Catalysed Allylic Substitution Using 2,8,14,20-Tetrapentylresorcinarenyl-Substituted Imidazolium Salts

Kaloglu M., SAHIN N., SEMERIL D., BRENNER E., MATT D., ÖZDEMİR İ., ...More

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol.2015, no.33, pp.7310-7316, 2015 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 2015 Issue: 33
  • Publication Date: 2015
  • Doi Number: 10.1002/ejoc.201501070
  • Journal Name: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.7310-7316
  • Keywords: Cavitands, Calixarenes, Carbenes, Copper, Allylic substitution, Regioselectivity, DERIVATIVES, ALKYLATION, STEREOCHEMISTRY, COMPLEXES, REGIOCHEMISTRY, REGIOCONTROL, ACETATES
  • Inonu University Affiliated: Yes

Abstract

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.