TY - JOUR
T1 - Benzimidazole-based N-heterocyclic carbene silver complexes as catalysts for the formation of carbonates from carbon dioxide and epoxides
AU - Nawaz, Zahid
AU - Ullah, Habib
AU - Gürbüz, Nevin
AU - Zafar, Muhammad Naveed
AU - Verpoort, Francis
AU - Tahir, Muhammad Nawaz
AU - Özdemir, Ismail
AU - Trovitch, Ryan J.
N1 - Funding Information: Z.N. gratefully acknowledges the Higher Education Commission of Pakistan (HEC) for research funding as an IRSIP fellow at Arizona State University (USA) and the Technological and Scientific Research Council of Turkey (TÜBİTAK) for Ph.D. research funding (2216 Research Fellowship Programme). This study was supported by İnönü University Research Fund (İÜ‐BAP: FBG-2019-1594). The author H.U. would also like to express their deep thanks to the State Key Lab of Advanced Technology for Materials Synthesis and Processing (Wuhan University of Technology) for financial support. H.U. expresses his deep appreciation to the Chinese Scholarship Council (CSC) for his Ph.D. study grant 2015GF012. Publisher Copyright: © 2022
PY - 2022/6
Y1 - 2022/6
N2 - 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.
AB - 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.
KW - Carbon dioxide insertion
KW - Cyclic carbonate
KW - Homogeneous catalysis
KW - N-heterocyclic carbene
KW - Silver complexes
UR - https://www.scopus.com/pages/publications/85134082695
UR - https://www.scopus.com/pages/publications/85134082695#tab=citedBy
U2 - 10.1016/j.mcat.2022.112369
DO - 10.1016/j.mcat.2022.112369
M3 - Article
SN - 2468-8231
VL - 526
JO - Molecular Catalysis
JF - Molecular Catalysis
M1 - 112369
ER -