N-Heterocyclic Carbene Metal Complexes: Synthesis, Properties and Applications, 2nd Edition

A special issue of Inorganics (ISSN 2304-6740). This special issue belongs to the section "Organometallic Chemistry".

Deadline for manuscript submissions: 31 January 2025 | Viewed by 627

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Department of Chemistry, Georgia State University, Atlanta, GA 30303, USA
Interests: organic synthesis; organometallic chemistry; asymmetric reactions; catalysis; heterocyclic chemistry
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Dear Colleagues,

N-heterocyclic carbenes (NHCs) are nitrogen-containing cyclic carbenes stabilized by one or two heteroatoms. Since the isolation and characterization of the first stable crystalline-free NHC by Arduengo in 1991, the interest in this class of compounds has dramatically increased. As the study of NHCs, their properties, and ability to coordinate with transition metals continues, reports on  the applications of NHC–metal complexes have attracted more researchers into the field. NHC–metal complexes can be formed with both soft and hard metal ions, leading to additional applications. NHC ligands have numerous advantages over conventional phosphine or nitrogen ligands, such as outstanding σ donor and poor π acceptor abilities; thus, they form stronger NHC–metal bonds. Many reports indicate that NHC–metal complexes have proven to be more effective in most catalytic reactions than, for example, metal–phosphine complexes. Transition metal–NHC complexes, due to the presence of d-orbitals and ability to change oxidation state, are among the most used in modern catalysis. A number of complexes have exhibited unusual physico-chemical properties and found applications in material science and electronics. Furthermore, NHC–metal complexes, particularly those of silver(I), gold(I), and palladium(II), have been identified as active antimicrobial and anticancer agents with bioactivities similar to or exceeding those of drugs that are currently on the market. Despite a number of stable NHCs and their metallic complexes now being commercially available, there are still open and constantly growing opportunities for this field of study due to their intrinsic structural diversity.

This Special Issue intends to cover the most recent advances in the field of N-heterocyclic carbene metal complexes. It includes the design and preparation of new NHC ligands and their coordination with transition metals, characterization, physico-chemical properties, application in catalytic reactions, material science, medicinal chemistry, polymers, and access to commercially valuable molecules, drugs, and natural products.

Dr. Kostiantyn Marichev
Guest Editor

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Keywords

  • NHC–metal complexes
  • σ-donors
  • ligand design
  • catalysis
  • polymers
  • antimicrobial and anticancer activity
  • magneto- and photochemistry

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Published Papers (1 paper)

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Research

12 pages, 2035 KiB  
Article
Catalytic Behavior of NHC–Silver Complexes in the Carboxylation of Terminal Alkynes with CO2
by Assunta D’Amato, Marco Sirignano, Francesco Viceconte, Pasquale Longo and Annaluisa Mariconda
Inorganics 2024, 12(11), 283; https://doi.org/10.3390/inorganics12110283 - 30 Oct 2024
Viewed by 139
Abstract
A number of N-heterocyclic carbene–silver compounds (NHCs)AgX were tested in the direct carboxylation of terminal alkynes using carbon dioxide as the C1 carbon feedstock. The reactions proceed at a pressure of 1 atm of CO2 at room temperature, in the presence of [...] Read more.
A number of N-heterocyclic carbene–silver compounds (NHCs)AgX were tested in the direct carboxylation of terminal alkynes using carbon dioxide as the C1 carbon feedstock. The reactions proceed at a pressure of 1 atm of CO2 at room temperature, in the presence of Cs2CO3, and using silver–NHC complexes as catalysts. Thus, phenylacetylene and several alkynes are converted to the corresponding propiolic acids in good to high conversions. The activity of the catalysts is strongly influenced by the substituents on the NHC backbone and the nature of the counterion. Specifically, the most active compound exhibits iodide as the counterion and is stabilized by a benzimidazole derivative. After 24 h of reaction, a quantitative conversion is obtained utilizing DMF as the solvent and phenylacetylene as the substrate. Full article
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Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Title: A Kinetic Study of the formation of a Tetradentate NCCN N-Heterocyclic Copp(II) Carbene Complex
Authors: Joseph P. Emerson
Affiliation: Mississippi State University, Mississippi State, United States

Title: Reactions of 1-Alkyl-3-phenylbenzimidazolium Salts with Ag2O: Formation of a Ring-Opening Formamide Derivative and a Ag Complex with an N-Heterocyclic Carbene Ligand
Authors: Satoshi Sakaguchi*, Takashi Higashino, Yudai Tasaki and Ryo Ichihara
Affiliation: Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University, Suita, Osaka 564-8680, Japan

Title: Catalytic behaviour of NHC-silver complexes in the carboxylation of terminal alkynes with CO2
Authors: Assunta D’Amato; Marco Sirignano; Francesco Viceconte; Pasquale Longo; Annaluisa Mariconda
Affiliation: Department of Basic and Applied Sciences, University of Basilicata, Via Dell’Ateneo Lucano, 10, 85100 Po-tenza, Italy
Abstract: A number of N-heterocyclic carbene-silver compounds (NHC)AgX were tested in the direct carboxylation of terminal alkynes using carbon dioxide as the C1 carbon feedstock. The reactions proceed at a pressure of 1 atm of CO2 at room temperature, in the presence of Cs2CO3, and using silver-NHC complexes as catalysts. Thus, phenylacetylene and several alkynes were converted to the corresponding propiolic acids in good to high yields. The activity of the catalysts is strongly influenced by the substituents on the NHC backbone and the nature of the counterion. Specifically, the most active compound exhibits iodide as the counterion and is stabilized by a benzimidazole derivative. After 24 hours of reaction, a quantitative yield is obtained utilizing DMF as the solvent and phenylacetylene as the substrate.

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