Dinuclear silver-bis(N-heterocyclic carbene) complexes: Synthesis, catalytic activity in propargylamine formation and computational studies

Atli D. D., Sen B.

JOURNAL OF COORDINATION CHEMISTRY, vol.74, no.14, pp.2289-2301, 2021 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 74 Issue: 14
  • Publication Date: 2021
  • Doi Number: 10.1080/00958972.2021.1972097
  • Journal Name: JOURNAL OF COORDINATION CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Metadex
  • Page Numbers: pp.2289-2301
  • Keywords: Bis(N-heterocyclic carbene), A(3)-Coupling, Propargylamine, Silver ion, DFT Calculations, N-HETEROCYCLIC CARBENE, ONE-POT SYNTHESIS, SILVER COMPLEX, A(3)-COUPLING REACTION, COUPLING REACTION, AG(I) COMPLEXES, EFFICIENT, ANTICANCER, ANTIBACTERIAL, CHEMISTRY
  • Dokuz Eylül University Affiliated: Yes

Abstract

Preparation of a series of 1,1 '-dialkyl-3,3 '-(2-methylenepropane-1,3-diyl)dibenzimidazolium salts (alkyl = ethyl, propyl, butyl) (2a-2c) and their dinuclear bis(N-heterocyclic carbene) silver complexes (3a-3c) is reported. The silver complexes were synthesized via in situ deprotonation with Ag2O in 67-74% yields. The structural definitions of the synthesized compounds were performed by H-1 NMR, C-13 NMR, elemental analysis, FT-IR and also LC-MSMS techniques (only for 3a-3c). The silver complexes were utilized for three-component coupling reactions of aldehydes, amines and alkynes (A(3)-coupling). It was found that increasing the chain length of the alkyl substituent on the N-heterocyclic carbene ligand led to increase in catalytic performance. 3c showed the highest activity with 81% yield and with TON of 27 for N,N-diethyl-3-phenylprop-2-yn-1-amine formation. Geometry optimization was performed and geometric parameters were calculated for the compounds. The theoretical harmonic vibration frequencies of molecules were computed by DFT/B3LYP methods for their optimized geometries.