Synthesis of sterically hindered N-benzyladamantyl substituted benzimidazol-2-ylidene palladium complexes and investigation of their catalytic activity in aqueous medium


Dehimat Z. I. , PAŞAHAN A. , Tebbani D., YAŞAR S. , ÖZDEMİR İ.

TETRAHEDRON, vol.73, no.40, pp.5940-5945, 2017 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 73 Issue: 40
  • Publication Date: 2017
  • Doi Number: 10.1016/j.tet.2017.08.037
  • Title of Journal : TETRAHEDRON
  • Page Numbers: pp.5940-5945
  • Keywords: N-heterocyclic carbene complex, Palladium, Suzuki coupling, Green chemistry, CROSS-COUPLING REACTIONS, HETEROCYCLIC CARBENE COMPLEXES, SUZUKI-MIYAURA REACTION, TRANSITION-METAL-COMPLEXES, LINKED AMPHIPHILIC POLYMER, PD-PEPPSI-IPENT, LIGAND-FREE, ROOM-TEMPERATURE, ASSEMBLED COMPLEX, ARYL CHLORIDES

Abstract

NHC-Pd-PEPPSI complexes with bulky benzyladamantyl substituted N-heterocyclic carbenes (NHC) were synthesized and characterized by NMR, HRMS, and micro analysis. These complexes were then used for Suzuki-Miyaura coupling reactions between aryl bromides and phenylboronic acid. With low catalyst, loading, all synthesized complexes rapidly catalyzed the Suzuki-Miyaura cross-coupling reaction in iPrOH/water (1:3 v/v) at room temperature in air. All palladium compounds were stable and had high catalytic activity for the Suzuki-Miyaura coupling reaction. (C) 2017 Elsevier Ltd. All rights reserved.