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Keywords = N-Heterocyclic carbene

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16 pages, 6618 KiB  
Review
N-Heterocyclic Carbene-Catalyzed Aerobic Oxidation of Aromatic Aldehydes into Carboxylic Acids: A Critical Review
by Alain Favre-Réguillon
Catalysts 2025, 15(8), 708; https://doi.org/10.3390/catal15080708 - 25 Jul 2025
Viewed by 475
Abstract
N-heterocyclic carbenes (NHCs) have demonstrated their versatility as catalysts for new activations and synthetic transformations of aldehydes. NHCs were originally applied in benzoin condensation and the Stetter reaction, while the development of new protocols under oxidative conditions has further expanded the potential of [...] Read more.
N-heterocyclic carbenes (NHCs) have demonstrated their versatility as catalysts for new activations and synthetic transformations of aldehydes. NHCs were originally applied in benzoin condensation and the Stetter reaction, while the development of new protocols under oxidative conditions has further expanded the potential of this methodology for the formation of carbon−carbon and carbon−heteroatom bonds. Among these reactions, NHCs are recognized as promising organocatalysts for the aerobic oxidation of aldehydes to carboxylic acids. However, to our knowledge, a comparison with other metal-free protocols has never been conducted. This review is intended to provide a perspective on aldehyde oxidation into the corresponding carboxylic acid catalyzed by NHCs, from its first practical description in 2009 until the beginning of 2025, and to compare it with other metal-free methods. Full article
(This article belongs to the Section Catalysis in Organic and Polymer Chemistry)
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12 pages, 2466 KiB  
Article
ROMP and Vinyl Polynorbornenes with Vanadium(III) and Nickel(II) diNHC Complexes
by Katarzyna Halikowska-Tarasek, Elwira Bisz, Dawid Siodłak, Błażej Dziuk and Wioletta Ochędzan-Siodłak
Int. J. Mol. Sci. 2025, 26(14), 6691; https://doi.org/10.3390/ijms26146691 - 12 Jul 2025
Viewed by 345
Abstract
The polymerization of norbornene can occur via ring-opening metathesis polymerization (ROMP) or vinyl-addition pathways, each yielding polynorbornene with distinct structures and properties. This study reports on the synthesis and catalytic application of a new class of vanadium(III) and nickel(II) complexes bearing N-heterocyclic [...] Read more.
The polymerization of norbornene can occur via ring-opening metathesis polymerization (ROMP) or vinyl-addition pathways, each yielding polynorbornene with distinct structures and properties. This study reports on the synthesis and catalytic application of a new class of vanadium(III) and nickel(II) complexes bearing N-heterocyclic carbene ligands, based on the IPr* framework, for the polymerization of norbornene. The vanadium(III) complexes, activated by diethylaluminum chloride and in the presence of ethyl trichloroacetate, showed activity in ROMP. In contrast, the nickel(II) complexes, activated by methylaluminoxane, exhibited catalytic activity toward vinyl-addition polymerization. Characterization by GPC, NMR, and FTIR confirmed the formation of both ring-opening metathesis polymerization and vinyl-type-derived polynorbornenes, with vinyl-type polymers showing significantly higher molecular weights. Structural variations in the N-heterocyclic carbene ligands, particularly the linker length between imidazole donors, were found to strongly influence polymer molecular weight and the morphology of polynorbornenes. Full article
(This article belongs to the Section Materials Science)
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9 pages, 1055 KiB  
Short Note
A Pyrene-Anchored Nickel N-Heterocyclic Carbene–Isoquinoline Complex Promotes CO2 Reduction
by Xue Chen, Li-Li Yu, Shu-Ying Chen, Tong Wang and Quan Zhou
Molbank 2025, 2025(3), M2035; https://doi.org/10.3390/M2035 - 8 Jul 2025
Viewed by 380
Abstract
In this study, on the basis of a previous report, a pyrene-anchored nickel complex was designed and synthesized via five steps. The NMR spectra of the synthesized complex were found to exhibit significant proton and carbon chemical shift anisotropy. Cyclic voltammetry spectra showed [...] Read more.
In this study, on the basis of a previous report, a pyrene-anchored nickel complex was designed and synthesized via five steps. The NMR spectra of the synthesized complex were found to exhibit significant proton and carbon chemical shift anisotropy. Cyclic voltammetry spectra showed that the introduction of pyrene slightly influenced the onset potential of CO2 reduction. Lastly, controlled-potential electrolysis experiments disclosed that a pyrene-anchored nickel carbene–isoquinoline (Ni−2) complex selectively converted CO2 into CH4 with a TON value of 2.3 h−1. Full article
(This article belongs to the Topic Heterocyclic Carbene Catalysis)
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20 pages, 6758 KiB  
Article
Novel Au(I)- and Ag(I)-NHC Complexes with N-Boc-Protected Proline as Potential Candidates for Neurodegenerative Disorders
by Jessica Ceramella, Assunta D’Amato, Francesca Procopio, Annaluisa Mariconda, Daniel Chavarria, Domenico Iacopetta, Francesco Ortuso, Pasquale Longo, Fernanda Borges and Maria Stefania Sinicropi
Int. J. Mol. Sci. 2025, 26(13), 6116; https://doi.org/10.3390/ijms26136116 - 25 Jun 2025
Viewed by 432
Abstract
Neurodegenerative diseases (NDDs), including Alzheimer’s disease (AD) and Parkinson’s disease (PD), are characterized by progressive neuronal dysfunction and loss and represent a significant global health challenge. Oxidative stress, neuroinflammation, and neurotransmitter dysregulation, particularly affecting acetylcholine (ACh) and monoamines, are key hallmarks of these [...] Read more.
Neurodegenerative diseases (NDDs), including Alzheimer’s disease (AD) and Parkinson’s disease (PD), are characterized by progressive neuronal dysfunction and loss and represent a significant global health challenge. Oxidative stress, neuroinflammation, and neurotransmitter dysregulation, particularly affecting acetylcholine (ACh) and monoamines, are key hallmarks of these conditions. The current therapeutic strategies targeting cholinergic and monoaminergic systems have some limitations, highlighting the need for novel approaches. Metallodrugs, especially ruthenium and platinum complexes, are gaining attention for their therapeutic use. Among metal complexes, gold(I) and silver(I) N-heterocyclic carbene (NHC) complexes exhibit several biological activities, but their application in NDDs, particularly as monoamine oxidase (MAO) inhibitors, remains largely unexplored. To advance the understanding of this field, we designed, synthesized, and evaluated the biological activity of a new series of Au(I) and Ag(I) complexes stabilized by NHC ligands and bearing a carboxylate salt of tert-butyloxycarbonyl (Boc)-N-protected proline as an anionic ligand. Through in silico and in vitro studies, we assessed their potential as acetylcholinesterase (AChE) and MAO inhibitors, as well as their antioxidant and anti-inflammatory properties, aiming to contribute to the development of potential novel therapeutic agents for NDD management. Full article
(This article belongs to the Special Issue Advances in Novel Anti-Alzheimer Drugs: Biological Target, Medicinal Chemistry and Formulation)
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17 pages, 3400 KiB  
Article
In Vitro Evaluation of Silver-NHC Complexes Against a Clinical Isolate of Acanthamoeba castellanii: Time- and Dose-Dependent Effects
by Zübeyda Akın-Polat, Neslihan Şahin, Shaima Hkiri, Bui Minh Thu Ly, İsmail Özdemir and David Sémeril
Inorganics 2025, 13(6), 204; https://doi.org/10.3390/inorganics13060204 - 18 Jun 2025
Viewed by 380
Abstract
The synthesis of a series of six chloro[N-alkyl-N-cinnamyl-benzimidazol-2-yliden]silver(I) complexes was successfully achieved, wherein allyl (3a), methoxymethyl (3b), benzyl (3c), 3-fluorobenzyl (3d), 4-fluorobenzyl (3e) and 4-methyl-benzyl (3f) substituents [...] Read more.
The synthesis of a series of six chloro[N-alkyl-N-cinnamyl-benzimidazol-2-yliden]silver(I) complexes was successfully achieved, wherein allyl (3a), methoxymethyl (3b), benzyl (3c), 3-fluorobenzyl (3d), 4-fluorobenzyl (3e) and 4-methyl-benzyl (3f) substituents were grafted on the benzimidazole ring. The isolated silver N-heterocyclic carbene (NHC) complexes were identified by microanalyses and mass spectrometry and characterized by FT-IR and NMR spectroscopic techniques. Conclusive evidence for the structures of complexes 3c and 3d was provided by single-crystal X-ray crystallography. The in vitro inhibitory activity of the six Ag-NHC complexes was tested against trophozoites and cysts of the pathogenic Acanthamoeba castellanii strain and the efficacy sequence is as follows: 3d > 3c > 3f > 3a > 3b > 3e. At a concentration of 100 µM in complexes 3c, 3d and 3f and after 72 h of incubation, 5.3, 3.2 and 6.3% A. castellanii trophozoite viabilities were observed, respectively. The utilization of elevated silver(I) drug concentrations, 1000 µM, resulted in the near-total eradication of pathogenic protozoa. Full article
(This article belongs to the Special Issue Metal Complexes Containing Bioactive Ligands: Structure and Biological Evaluation)
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48 pages, 13615 KiB  
Review
Overview of Some Second- and Third-Row Late Transition Metal Pincer-Type N-Heterocyclic Carbene Complexes: Synthesis, Optical Properties, and Applications
by Dong-Ling Kuang, Ka-Kit Li, Lai-Hon Chung, Jun He and Chun-Yuen Wong
Molecules 2025, 30(12), 2640; https://doi.org/10.3390/molecules30122640 - 18 Jun 2025
Viewed by 494
Abstract
N-heterocyclic carbenes (NHCs) were first isolated as stable species by Arduengo in 1991. Since then, they have expanded the boundaries of carbene chemistry and sparked extensive research. Utilizing NHCs to modify the electronic properties of transition metal complexes represents a significant advancement [...] Read more.
N-heterocyclic carbenes (NHCs) were first isolated as stable species by Arduengo in 1991. Since then, they have expanded the boundaries of carbene chemistry and sparked extensive research. Utilizing NHCs to modify the electronic properties of transition metal complexes represents a significant advancement in the field. Pincer-type NHCs, which occupy half or more of the vacant sites on metal centers, typically result in structurally well-defined molecular platforms with specific active sites for a variety of applications. This review provides an overview of late transition metal complexes based on pincer-type NHCs, discussing their synthetic strategies, reactivities, and electronic properties, as well as their applications. Additionally, some perspectives will be presented to highlight future directions in this rapidly growing field. Full article
(This article belongs to the Special Issue Featured Reviews in Organometallic Chemistry, 2nd Edition)
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14 pages, 1591 KiB  
Article
Synergistic Control of Liquid Crystallinity and Phosphorescence in Gold(I) Complexes via Strategic Alkyl Chain Design
by Arushi Rawat, Kohsuke Matsumoto, Ganesan Prabusankar and Osamu Tsutsumi
Crystals 2025, 15(6), 554; https://doi.org/10.3390/cryst15060554 - 10 Jun 2025
Viewed by 1266
Abstract
Liquid crystals exhibit unique properties that can be tailored in response to external stimuli. Significant research is directed toward the development of luminescent materials exhibiting liquid crystallinity for various applications. The present work reports Au(I) complexes featuring N-heterocyclic carbene and phenyl acetylide ligands. [...] Read more.
Liquid crystals exhibit unique properties that can be tailored in response to external stimuli. Significant research is directed toward the development of luminescent materials exhibiting liquid crystallinity for various applications. The present work reports Au(I) complexes featuring N-heterocyclic carbene and phenyl acetylide ligands. Metal complexes enable the utilization of the triplet excitons through their inherent spin–orbit coupling, promoting intersystem crossing from singlet (Sn) to triplet (Tn) states to observe room-temperature phosphorescence (RTP). The strong bonds between carbene and Au enhance the thermal stability, and the substituted benzimidazole ring alters the thermodynamic and photophysical properties of the complexes. Incorporating the acetylide ligands with long alkoxy chains led to the formation of liquid crystalline (LC) phases, which exhibited stability over a wide temperature range. Additionally, the luminescence behavior was affected by the ethynyl ligands, and high quantum yields of RTP were observed. This study establishes the development of LC Au(I) complexes with a thermodynamically stable LC mesophase over a wide temperature range for applications in the field of light-emitting functional materials. Full article
(This article belongs to the Special Issue State-of-the-Art Liquid Crystals Research in Japan (2nd Edition))
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14 pages, 1353 KiB  
Article
One-Pot Syntheses and Characterization of Group VI Carbonyl NHC Coordination Compounds
by Zala Stopar, Evelin Gruden, Melita Tramšek and Gašper Tavčar
Molecules 2025, 30(11), 2433; https://doi.org/10.3390/molecules30112433 - 2 Jun 2025
Viewed by 549
Abstract
The reactions of N-heterocyclic carbenes (IMesNHC and IPrNHC) with transition metal carbonyls of group VI (Cr(CO)6, Mo(CO)6, and W(CO)6) were carried out in acetonitrile in simple one-pot syntheses and led to the formation of the coordination [...] Read more.
The reactions of N-heterocyclic carbenes (IMesNHC and IPrNHC) with transition metal carbonyls of group VI (Cr(CO)6, Mo(CO)6, and W(CO)6) were carried out in acetonitrile in simple one-pot syntheses and led to the formation of the coordination compounds IMesNHC–Cr(CO)5 (1a), IMesNHC–Mo(CO)5 (2a), IMesNHC–W(CO)5 (3a), IPrNHC–Cr(CO)5 (1b), IPrNHC–Mo(CO)5 (2b), and IPrNHC–W(CO)5 (3b). With the exception of 1b, the coordination compounds were formed selectively and in high yields. The method represents an effective and easy-to-perform alternative to the previously described methods for NHC–M(CO)5 (M = Cr, Mo, W). All prepared compounds were characterized by NMR and Raman spectroscopy. Compounds 1a, 2a, 3a, and 2b were also crystallized and structurally characterized by X-ray structure analysis. Finally, the structural features of all compounds were compared with DFT calculations of structurally optimized coordination compounds. Full article
(This article belongs to the Special Issue Featured Papers in Organometallic Chemistry—2nd Edition)
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12 pages, 1551 KiB  
Article
Experimental Attempts at and Theoretical Study of the Thermal Generation of o-Carborane-Supported N-Heterocyclic Carbenes
by Mei-Juan Liang, Ke-Cheng Chen, Zhongzheng Cui, Yan-Chang Zhou, Yan Wang, Fan Qi and Xu-Qiong Xiao
Inorganics 2025, 13(6), 179; https://doi.org/10.3390/inorganics13060179 - 25 May 2025
Viewed by 558
Abstract
N-Heterocyclic carbenes (NHCs) have been widely utilized over the past three decades due to their broad applications, yet synthetic methods for their preparation remain limited. A promising approach for NHC generation involves the thermolysis of NHC adducts. Herein, we report the synthesis of [...] Read more.
N-Heterocyclic carbenes (NHCs) have been widely utilized over the past three decades due to their broad applications, yet synthetic methods for their preparation remain limited. A promising approach for NHC generation involves the thermolysis of NHC adducts. Herein, we report the synthesis of NHC pentafluorobenzene adducts featuring an o-carboranyl group in the backbone (2), which, unlike previously studied systems, resists thermal decomposition. Density functional theory (DFT) calculations were used to investigate the discrepancy, revealing that the decomposition reaction is kinetically controlled. For widely studied NHC systems like IMes and SIMes, the activation barriers were calculated to be 246.3 kJ/mol and 267.3 kJ/mol, respectively, aligning with reactions requiring heating. In contrast, the o-carborane system exhibited a significantly higher barrier of 320.5 kJ/mol, primarily due to the structural influence of the o-carborane backbone. Further analysis indicates that delocalization of π-electrons from the backbone into the NHC’s p-orbitals lowers the activation barrier, whereas delocalization into an exo-NHC ring increases it. These findings provide new insights into the thermal generation of NHCs and we hope it can offer guidance for future NHC design and synthesis. Full article
(This article belongs to the Topic Heterocyclic Carbene Catalysis)
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18 pages, 5022 KiB  
Review
Searching for New Gold(I)-Based Complexes as Anticancer and/or Antiviral Agents
by Paola Checconi, Annaluisa Mariconda, Alessia Catalano, Jessica Ceramella, Michele Pellegrino, Stefano Aquaro, Maria Stefania Sinicropi and Pasquale Longo
Molecules 2025, 30(8), 1726; https://doi.org/10.3390/molecules30081726 - 11 Apr 2025
Viewed by 902
Abstract
Approaches capable of simultaneously treating cancer and protecting susceptible patients from lethal infections are highly desirable, although they prove challenging. Taking inspiration from the well-known anticancer platinum complexes, successive studies about the complexation of organic compounds with other late transition metals, such as [...] Read more.
Approaches capable of simultaneously treating cancer and protecting susceptible patients from lethal infections are highly desirable, although they prove challenging. Taking inspiration from the well-known anticancer platinum complexes, successive studies about the complexation of organic compounds with other late transition metals, such as silver, gold, palladium, rhodium, ruthenium, iridium, and osmium, have led to remarkable anticancer activities. Among the numerous chemical moieties studied, N-heterocyclic carbenes (NHCs) have revealed very attractive activities due to their favorable chemical properties. Specifically, gold–NHC complexes emerged as some of the most active complexes acting as antitumor agents. On the other hand, some recent studies have highlighted the involvement of these complexes in antiviral research as well. The well-known gold-based, orally available complex auranofin approved by the Food and Drug Administration (FDA) for the treatment of rheumatoid arthritis has been suggested as a repositioned drug for both cancer and viral infections. In the era of the COVID-19 pandemic, the most interesting goal could be the discovery of gold–NHC complexes as dual antiviral and anticancer agents. In this review, the most recent studies regarding the anticancer and antiviral activities of gold(I)–NHC complexes will be analyzed and discussed, offering an interesting insight into the research in this field. Full article
(This article belongs to the Special Issue Exclusive Feature Papers in Inorganic Chemistry, 3rd Edition)
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12 pages, 3812 KiB  
Article
Hydroxyamide-Functionalized Azolium Anchored on Merrifield Resin for Enantioselective Ir-Catalyzed Reduction of Ketones with Silane
by Satoshi Sakaguchi, Masamune Koyabu and Kazuki Inui
Catalysts 2025, 15(4), 303; https://doi.org/10.3390/catal15040303 - 24 Mar 2025
Viewed by 498
Abstract
Polystyrene-supported chiral hydroxyamide-functionalized benzimidazolium chloride was synthesized by reacting Merrifield resin with a substituted-azole derived from (S)-leucinol. The combination of [IrCl(cod)]2 and the resulting polymer-supported N-heterocyclic carbene (NHC) ligand precursor catalyzed the enantioselective reduction of ketones using (EtO)2 [...] Read more.
Polystyrene-supported chiral hydroxyamide-functionalized benzimidazolium chloride was synthesized by reacting Merrifield resin with a substituted-azole derived from (S)-leucinol. The combination of [IrCl(cod)]2 and the resulting polymer-supported N-heterocyclic carbene (NHC) ligand precursor catalyzed the enantioselective reduction of ketones using (EtO)2MeSiH under heterogeneous reaction conditions via a pre-mixing reaction procedure. Additionally, the solid-state resin could be easily recovered through simple filtration and the catalyst system’s reusability was evaluated. Full article
(This article belongs to the Special Issue Heterogeneous Catalysis Towards a Sustainable Future)
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11 pages, 2106 KiB  
Article
Clicked H-Shaped Arylopeptoids
by Zein El Abidine Chamas, Ayman Akhdar, Florence Charnay-Pouget, Sophie Faure and Arnaud Gautier
Molecules 2025, 30(3), 724; https://doi.org/10.3390/molecules30030724 - 5 Feb 2025
Viewed by 551
Abstract
This study presents a tentative synthesis of supported H-shaped and ladder-type compounds. If the ladders were not accessible, probably due to distance misfits between the reactive centers, a facile method for the synthesis of H-shaped N-alkylated aminomethyl oligobenzamides, i.e., arylopeptoids by on-resin [...] Read more.
This study presents a tentative synthesis of supported H-shaped and ladder-type compounds. If the ladders were not accessible, probably due to distance misfits between the reactive centers, a facile method for the synthesis of H-shaped N-alkylated aminomethyl oligobenzamides, i.e., arylopeptoids by on-resin homodimerization via the Copper(I)-Catalyzed-Alkyne-Azide-Cycloaddition (CuAAC) reaction is reported. While successful, a synthetic bottleneck was identified for further oligomer elongation due to congestion when the ligation occurs on solid support. However, this issue was effectively addressed using an elongated oligomer to conduct inter-strand cross-linking. Further CuAAC functionalization could be performed after elongation with additional alkyne groups to enhance diversity. Full article
(This article belongs to the Section Organic Chemistry)
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16 pages, 1172 KiB  
Article
Mechanochemistry to Form Substituted Imidazoles, Imidazolium Salts and NHC–Gold Complexes with Fluorine-Containing Groups
by Chloé Salis, Sabrina Mohammedi, Lucia Turazza, Yuna Blandin, Maritie Garnier, Catherine Hemmert, Michel Baltas and Heinz Gornitzka
Molecules 2025, 30(3), 522; https://doi.org/10.3390/molecules30030522 - 24 Jan 2025
Viewed by 1476
Abstract
Synthesis of organometallic compounds has had an enormous impact on medicine. In this context, gold complexes are gaining much interest since the discovery of the cytotoxic effect of cisplatin. On the other hand, in the last two decades, the mechanochemical synthetic approaches have [...] Read more.
Synthesis of organometallic compounds has had an enormous impact on medicine. In this context, gold complexes are gaining much interest since the discovery of the cytotoxic effect of cisplatin. On the other hand, in the last two decades, the mechanochemical synthetic approaches have been developed considerably demonstrating that they could also be a powerful tool enabling environmentally benign and sustainable synthesis of metal complexes. The present work focuses on mechanochemical synthesis of precursors and gold–NHC complexes of type NHCAuCl and [AubisNHC]+. The mechanochemical approach has been studied to afford four substituted imidazoles, eight imidazolium salts and six NHCAuCl and one [AubisNHC]+. Substituted imidazoles were obtained with yields varying between 29–99%. Five imidazolium salts bearing aliphatic carbon atoms were obtained, with yields from 46–81%. It is important to notice that the reaction can follow the aging process giving rise to imidazolium salts in very good yields. Concerning the gold(I) complexes, for the first time, six mono NHC complexes of type NHCAuCl have been synthesized, five of them with yields varying between 41–83%. Finally, compound 19 [AubisNHC]+ has been obtained not only by transmetallation, but most gratifyingly through direct metalation in 73% yield. Full article
(This article belongs to the Section Organometallic Chemistry)
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24 pages, 5030 KiB  
Article
EtIDip (EtIPr)—Synthesis, Characterisation and Reactivity of a Robust, Backbone-Modified N-Heterocyclic Carbene and Group 13 Element Complexes
by Huanhuan Dong, Albert Martinez-Segura, Riley W. Kelehan, Connor Bourne, Aidan P. McKay, Alexandra M. Z. Slawin, David B. Cordes and Andreas Stasch
Inorganics 2025, 13(1), 27; https://doi.org/10.3390/inorganics13010027 - 17 Jan 2025
Viewed by 1080
Abstract
We report the synthesis, characterisation and reactivity of the stable imidazol-2-ylidene EtIDip (EtIPr), {EtCN(Dip)}2C:, Dip = 2,6-iPr2C6H3, as a chemically robust alternative to IDip (IPr), {HCN(Dip)}2C:. The N-heterocyclic [...] Read more.
We report the synthesis, characterisation and reactivity of the stable imidazol-2-ylidene EtIDip (EtIPr), {EtCN(Dip)}2C:, Dip = 2,6-iPr2C6H3, as a chemically robust alternative to IDip (IPr), {HCN(Dip)}2C:. The N-heterocyclic carbene EtIDip could be further converted to the oxidised species [EtIDipCl]Cl, EtIDipF2, EtIDipO, and EtIDipSe, and the group 13 element complexes EtIDipEX3, with E = B, X = Br; E = Al, X = I; E = Ga, X = I; E = Al, X = H. The properties of the EtIDip and IDip ligands are compared and the molecular structures of (DipNCEt)2, [EtIDipH]Cl, [EtIDipH]I, EtIDip, [EtIDipCl]Cl, EtIDipF2, EtIDipO, EtIDipBBr3, EtIDipAlI3, EtIDipGaI3, and EtIDipAlH3 have been determined. Full article
(This article belongs to the Special Issue Development and Applications of Sterically Demanding Ligands in Main Group Chemistry)
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11 pages, 1159 KiB  
Article
Reactions of 1-Alkyl-3-phenylbenzimidazolium Salts with Ag2O: The Formation of a Ring-Opening Formamide Derivative and a Ag Complex with an N-heterocyclic Carbene Ligand
by Satoshi Sakaguchi, Takashi Higashino, Yudai Tasaki, Ryo Ichihara and Tatsuo Yajima
Inorganics 2025, 13(1), 18; https://doi.org/10.3390/inorganics13010018 - 10 Jan 2025
Viewed by 895
Abstract
This study investigated the reactions of 1-alkyl-3-phenylbenzimidazolium salts with Ag2O. It was found that the selectivity of the reaction products was influenced by the N-alkyl substituent on the azolium ring. For example, treating 1-methyl-3-phenylbenzimidazolium iodide (2) with Ag [...] Read more.
This study investigated the reactions of 1-alkyl-3-phenylbenzimidazolium salts with Ag2O. It was found that the selectivity of the reaction products was influenced by the N-alkyl substituent on the azolium ring. For example, treating 1-methyl-3-phenylbenzimidazolium iodide (2) with Ag2O for 24 h produced the ring-opening formamide derivative N-[2-(phenylamino)phenyl]-N-methylformamide (2b) in an 85% yield. In contrast, the reaction of 1-benzyl-3-phenylbenzimidazolium chloride (3) with Ag2O under the same conditions yielded the corresponding N-heterocyclic carbene (NHC)–Ag complex (1-benzyl-3-phenylbenzimidazol-2-ylidene) silver(I) chloride (3a) in an 86% yield. Furthermore, the corresponding monodentate NHC–Au complex 2c could be synthesized by allowing 2 to react with AuCl(SMe2) in the presence of Ag2O. Full article
(This article belongs to the Special Issue N-Heterocyclic Carbene Metal Complexes: Synthesis, Properties and Applications, 2nd Edition)
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