Benzimidazole-based N-heterocyclic carbene silver complexes as catalysts for the formation of carbonates from carbon dioxide and epoxides

Zahid Nawaz, Habib Ullah, Nevin Gürbüz, Muhammad Naveed Zafar, Francis Verpoort, Muhammad Nawaz Tahir, Ismail Özdemir, Ryan J. Trovitch

Research output: Contribution to journalArticlepeer-review

Abstract

A series of left-to-right inequivalent 1,3-disubstituted benzimidazolium halide pro-ligands having the general formula [RBNHCCH2OxMe][X] (R = 3-Me-Bn, 3,5-Me2-Bn, 2,4,6-Me3-Bn, 2,3,5,6-Me4-Bn, 2,3,4,5,6-Me5-Bn, 3,4,5-(OMe)3-Bn, or 4-tBu-Bn; X = Cl, Br) were synthesized by the alkylation of 1-((3-methyloxetan-3-yl)methyl)benzimidazole. The corresponding Ag complexes, (RBNHCCH2OxMe)AgX, were prepared following pro-ligand addition to Ag2O. These compounds were characterized using spectroscopic techniques such as FT-IR, NMR spectroscopy, and single-crystal X-ray diffraction. The solid-state structure of (3-Me-BnBNHCCH2OxMe)AgCl revealed a linear monomer while [(2,4,6-Me3-BnBNHCCH2OxMe)AgCl]2 was found to exist as a dimer with pseudo trigonal planar geometry about each metal center. The synthesized (RBNHCCH2OxMe)AgX complexes were found to be efficient for the addition of carbon dioxide to epoxides to yield value-added cyclic carbonates at ambient pressure. Amongst the investigated complexes, the bimetallic complex [(2,4,6-Me3-BnBNHCCH2OxMe)AgCl]2 was found to be the most active for CO2 insertion, exhibiting favorable activity when compared to known NHC complexes.

Original languageEnglish (US)
Article number112369
JournalMolecular Catalysis
Volume526
DOIs
StatePublished - Jun 2022

Keywords

  • Carbon dioxide insertion
  • Cyclic carbonate
  • Homogeneous catalysis
  • N-heterocyclic carbene
  • Silver complexes

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology
  • Physical and Theoretical Chemistry

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