N-heterocyclic carbene based ruthenium complexes for selective beta-C(sp(3))-H functionalization of N-fused saturated cyclic amines

Kaloglu N.

TETRAHEDRON, vol.75, no.15, pp.2265-2272, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 75 Issue: 15
  • Publication Date: 2019
  • Doi Number: 10.1016/j.tet.2018.12.049
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2265-2272
  • Inonu University Affiliated: Yes

Abstract

Herein, a series of new ruthenium(II) complexes with the general molecular formula [RuCl2(arene)(NHC)], (arene = eta(6)-p-cymene, NHC = N-heterocyclic carbene) were synthesized from in situ prepared silver(I)-NHCs by the transmetallation method. These complexes were fully characterized by analytical and spectral methods. Ruthenium(11) complexes were tested as promising catalyst for selective B-C(sp(3))-H functionalization of N-methylpiperidine with various aldehydes through hydrogen transfers in presence of external acidic additive. These eco-friendly cross-dehydrogenative couplings enable the production of C(3)-alkylated N-methylpiperidine derivatives without enamines with only carbon dioxide and water as benign by-product. (C) 2019 Elsevier Ltd. All rights reserved.