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

doi:10.1016/j.mcat.2022.112369

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

Molecular Sciences, School of (SMS)

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

A series of left-to-right inequivalent 1,3-disubstituted benzimidazolium halide pro-ligands having the general formula [^RBNHC^CH2OxMe][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, (^RBNHC^CH2OxMe)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-BnBNHC^CH2OxMe)AgCl revealed a linear monomer while [(^2,4,6-Me3-BnBNHC^CH2OxMe)AgCl]₂ was found to exist as a dimer with pseudo trigonal planar geometry about each metal center. The synthesized (^RBNHC^CH2OxMe)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-BnBNHC^CH2OxMe)AgCl]₂ was found to be the most active for CO₂ insertion, exhibiting favorable activity when compared to known NHC complexes.

Original language	English (US)
Article number	112369
Journal	Molecular Catalysis
Volume	526
DOIs	https://doi.org/10.1016/j.mcat.2022.112369
State	Published - 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

Access to Document

10.1016/j.mcat.2022.112369

Cite this

@article{7093d9ef7a0c483ab0d8652a6c3f9d0f,

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

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.",

keywords = "Carbon dioxide insertion, Cyclic carbonate, Homogeneous catalysis, N-heterocyclic carbene, Silver complexes",

author = "Zahid Nawaz and Habib Ullah and Nevin G{\"u}rb{\"u}z and Zafar, {Muhammad Naveed} and Francis Verpoort and Tahir, {Muhammad Nawaz} and Ismail {\"O}zdemir and Trovitch, {Ryan J.}",

note = "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 (T{\"U}BİTAK) for Ph.D. research funding (2216 Research Fellowship Programme). This study was supported by İn{\"o}n{\"u} University Research Fund (İ{\"U}‐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: {\textcopyright} 2022",

year = "2022",

month = jun,

doi = "10.1016/j.mcat.2022.112369",

language = "English (US)",

volume = "526",

journal = "Molecular Catalysis",

issn = "2468-8231",

publisher = "Elsevier BV",

}

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

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UR - http://www.scopus.com/inward/citedby.url?scp=85134082695&partnerID=8YFLogxK

U2 - 10.1016/j.mcat.2022.112369

DO - 10.1016/j.mcat.2022.112369

M3 - Article

AN - SCOPUS:85134082695

SN - 2468-8231

VL - 526

JO - Molecular Catalysis

JF - Molecular Catalysis

M1 - 112369

ER -

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

Abstract

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CCDC 2056036: Experimental Crystal Structure Determination

CCDC 2056037: Experimental Crystal Structure Determination

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

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 2056036: Experimental Crystal Structure Determination

CCDC 2056037: Experimental Crystal Structure Determination

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