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N-heterocyclic Carbenes (NHC) and NHC-Metal Complexes: Preparation, Characterization and Applications...
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N-heterocyclic Carbenes (NHC) and NHC-Metal Complexes: Preparation, Characterization and Applications in Modern Catalysis

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalysis in Organic and Polymer Chemistry".

Deadline for manuscript submissions: 1 April 2025 | Viewed by 7812

Special Issue Editor

Dr. Tomasz K. Olszewski

E-Mail Website
Guest Editor
Department of Physical and Quantum Chemistry, Faculty of Chemistry, Wroclaw University of Science and Technology, Wybrzeze Wyspianskiego 29, 50-370 Wroclaw, Poland
Interests: catalysis; olefin metathesis; NHC complexes; chemistry of hetero-organic compounds; carbohydrate chemistry; asymmetric synthesis; green chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Since the breakthrough isolation of “free” N-Heterocyclic carbene (NHC) in the 1990’s by the Arduengo group, NHCs have been established as an almost indispensable class of ligands for homogeneous and heterogeneous catalysis, with multiple catalytic applications reported thus far. Especially, the steric modularity and electronic effects associated with the metal complexes has made the NHCs excellent candidates for designing new metal catalysts for catalytic transformations. In that respect, the synthesis of catalysts based on, e.g., ruthenium, palladium, or more affordable metals such as cooper and silver, are still eagerly sought.

This Special Issue of Catalysts aims to provide an overview of the latest progress in the preparation, characterization, and application of N-heterocyclic carbenes and NHC-metal complexes in modern catalytic processes. Experimental contributions, including full papers, communications, as well as reviews, describing the synthesis and applications of N-heterocyclic carbenes and NHC-metal complexes are welcome.

As a Guest Editor, it is my great pleasure to invite all researchers working in the flourishing, exciting, and broad field of N-heterocyclic carbene chemistry to contribute to this Special Issue of Catalysts.

Dr. Tomasz K. Olszewski
Guest Editor

Manuscript Submission Information

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Keywords

  • N-Heterocyclic Carbene
  • NHC
  • NHC-metal based complexes
  • NHC ligands
  • catalysis
  • heterogenous catalysis
  • homogenous catalysis
  • olefin metathesis
  • immobilized NHC based catalysts
  • catalytic cross-coupling reactions

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Published Papers (4 papers)

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Research

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13 pages, 3059 KiB  
Article
Tetranuclear N-Heterocyclic Carbene Palladium Acetate—The Fast-Initiating Precatalyst of Suzuki Coupling
by Sylwia Ostrowska, Szymon Rogalski, Maciej Kubicki and Cezary Pietraszuk
Catalysts 2024, 14(11), 836; https://doi.org/10.3390/catal14110836 - 20 Nov 2024
Viewed by 962
Abstract
A tetranuclear N-heterocyclic palladium carbene acetate, characterised by a [Pd]/[NHC] = 2/1 ratio, was synthesised and shown to be catalytically active in Suzuki coupling. Single crystal XRD studies of the complex revealed its unprecedented geometry, with the presence of three coordinated palladium [...] Read more.
A tetranuclear N-heterocyclic palladium carbene acetate, characterised by a [Pd]/[NHC] = 2/1 ratio, was synthesised and shown to be catalytically active in Suzuki coupling. Single crystal XRD studies of the complex revealed its unprecedented geometry, with the presence of three coordinated palladium centres. The catalytic activity of the complex is significantly higher than that of analogues containing the same N-heterocyclic carbene ligand. Preliminary studies have been carried out to determine the catalytic properties of the complex. Full article
(This article belongs to the Special Issue N-heterocyclic Carbenes (NHC) and NHC-Metal Complexes: Preparation, Characterization and Applications in Modern Catalysis)
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13 pages, 4656 KiB  
Article
Tuning the Latency by Anionic Ligand Exchange in Ruthenium Benzylidene Phosphite Complexes
by Nebal Alassad, Ravindra S. Phatake, Mark Baranov, Ofer Reany and N. Gabriel Lemcoff
Catalysts 2023, 13(11), 1411; https://doi.org/10.3390/catal13111411 - 2 Nov 2023
Cited by 1 | Viewed by 2648
Abstract
Recently discovered cis-dichloro benzylidene phosphite complexes are latent catalysts at room temperature and exhibit exceptional thermal and photochemical activation behavior in olefin metathesis reactions. Most importantly, the study of these catalysts has allowed their introduction in efficient 3-D printing applications of ring-opening [...] Read more.
Recently discovered cis-dichloro benzylidene phosphite complexes are latent catalysts at room temperature and exhibit exceptional thermal and photochemical activation behavior in olefin metathesis reactions. Most importantly, the study of these catalysts has allowed their introduction in efficient 3-D printing applications of ring-opening metathesis derived polymers and the control of chromatically orthogonal chemical processes. Moreover, their combination with plasmonic Au-nanoparticles has given rise to novel smart materials that are responsive to light. Given the importance of the ligand shell in the initiation and reactivity behavior of this family of complexes, we set out to investigate the effect of anionic ligand exchange. Thus, we report herein two new ruthenium benzylidene benzylphosphite complexes where the chloride anionic ligands have been replaced by bromide and iodide anions (cis-Ru-Phos-Br2 & cis-Ru-Phos-I2). The thermal and photochemical activations of these dormant catalysts in a variety of ring-closing and ring-opening metathesis polymerization (RCM and ROMP) reactions were thoroughly studied and compared with the previously known chloride precatalyst. Photochemical RCM studies provided similar results, especially in non-hindered reactions, with the UV-A wavelength being the best in all cases. On the other hand, the thermal activation profile exposed that the anionic ligand significantly affects reactivity. Notably, cis-Ru-Phos-I2 disclosed particularly impressive initiation efficiency compared to the other members of the family. Full article
(This article belongs to the Special Issue N-heterocyclic Carbenes (NHC) and NHC-Metal Complexes: Preparation, Characterization and Applications in Modern Catalysis)
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Review

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12 pages, 2119 KiB  
Review
Natural Chiral Ligand Strategy: Metal-Catalyzed Reactions with Ligands Prepared from Amino Acids and Peptides
by Benjamin W. Gung, Cole Kubesch and Gavriella Bernstein
Catalysts 2024, 14(11), 813; https://doi.org/10.3390/catal14110813 - 12 Nov 2024
Viewed by 941
Abstract
Amino acids and peptides are readily available biomolecules and can function as chiral ligands for transition metal catalysis. An example is the copper complex catalyzed 1,4-addition of dialkylzinc to acyclic enones, which employs peptide ligands. This review provides a dataset of amino acids [...] Read more.
Amino acids and peptides are readily available biomolecules and can function as chiral ligands for transition metal catalysis. An example is the copper complex catalyzed 1,4-addition of dialkylzinc to acyclic enones, which employs peptide ligands. This review provides a dataset of amino acids and peptides reported in the literature proving to be effective ligands for metal-centered catalysts. Several parameters were highlighted, including amino acid combination, metal atoms, carboxyl and amino protecting groups, modification of natural amino acids, and the mechanism of catalysis. Along with analyzing physical-chemical properties, the SMILES representation for each amino acid and/or peptide was generated and made available online, providing an easy-to-use means of training machine learning models. This review offers an opportunity for the development of more efficient peptide ligands for enantioselective metal-centered catalysts. The available online dataset is a reliable manually curated table, it enables the benchmark for comparison of new terminal functional groups. Moreover, the review provides insight into the structures of the more successful peptide ligands and can be used as the foundation for the development of the next generation of peptide-based chiral ligands. Full article
(This article belongs to the Special Issue N-heterocyclic Carbenes (NHC) and NHC-Metal Complexes: Preparation, Characterization and Applications in Modern Catalysis)
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45 pages, 16087 KiB  
Review
NHC-Catalyzed Reaction of Aldehydes for C(sp2)–O Bond Formation
by Yousuke Yamaoka and Hideto Miyabe
Catalysts 2024, 14(4), 219; https://doi.org/10.3390/catal14040219 - 22 Mar 2024
Cited by 2 | Viewed by 2333
Abstract
In the past few decades, N-heterocyclic carbenes (NHCs) have opened the new field of organocatalysis in synthetic organic chemistry. This review highlights the dramatic progress in the field of NHC-catalyzed C–O bond formation based on the activation of aldehyde C(sp2)–H [...] Read more.
In the past few decades, N-heterocyclic carbenes (NHCs) have opened the new field of organocatalysis in synthetic organic chemistry. This review highlights the dramatic progress in the field of NHC-catalyzed C–O bond formation based on the activation of aldehyde C(sp2)–H bonds. The oxidative and redox transformations for the synthesis of various molecules with structural diversity and complexity are summarized. Furthermore, new methods and strategies for NHC catalysis are emerging continuously; thus, cooperative catalysis with Brønsted acid, hydrogen-bonding catalyst, transition-metal catalyst, and photocatalyst are also described. Full article
(This article belongs to the Special Issue N-heterocyclic Carbenes (NHC) and NHC-Metal Complexes: Preparation, Characterization and Applications in Modern Catalysis)
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