Palladium(II)-N-heterocyclic carbene-catalyzed direct C2-or C5-arylation of thiazoles with aryl bromides


KALOĞLU M. , ÖZDEMİR İ.

TETRAHEDRON, vol.74, no.23, pp.2837-2845, 2018 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 74 Issue: 23
  • Publication Date: 2018
  • Doi Number: 10.1016/j.tet.2018.03.026
  • Title of Journal : TETRAHEDRON
  • Page Numbers: pp.2837-2845
  • Keywords: N-Heterocyclic carbene, Benzimidazolium halide, Palladium, Thiazole, Direct arylation, CROSS-COUPLING REACTIONS, COMPLEXES HIGHLY EFFICIENT, C-H ARYLATION, PYRROLE DERIVATIVES, ROOM-TEMPERATURE, BOND FORMATION, HETEROARENES, IMIDAZOLE, OXAZOLE, FUNCTIONALIZATION

Abstract

Herein we report a series of new benzimidazolium chlorides as N-heterocyclic carbene (NHC) ligand and their corresponding palladium(II)-NHC complexes with the general formula [PdCl2(NHC)(2)] were synthesized. All new compounds were characterized by H-1 NMR, C-13 NMR, IR spectroscopy and elemental analysis techniques. The catalytic activity of palladium(II)-NHC complexes was investigated in the direct C2- or C5-arylation of thiazoles with aryl bromides in presence of palladium(II)-NHC at 150(degrees)C for 1 h. These complexes exhibited the good catalytic performance for the direct arylation of thiazoles. The arylation of thiazoles regioselectively produced C2- or C5-arylated thiazoles in moderate to high yields. (C) 2018 Published by Elsevier Ltd.