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Journal articles on the topic 'Carbène NHC'

Author: Grafiati

Published: 8 June 2024

Last updated: 31 July 2025

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1

Alauddin, Mohammad, and Mazharul M. Islam. "A computational characterization of N-heterocyclic carbenes for catalytic and nonlinear optical applications." Zeitschrift für Naturforschung B 79, no. 4 (2024): 215–23. http://dx.doi.org/10.1515/znb-2023-0092.

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Abstract Very recently, N-heterocyclic carbenes (NHCs) have found a wide range of applications in the fields of catalysis and nonlinear optics. Herein, we have employed 1,3-bis-(1(S)-benzyl)-4,5-dihydro-imidazol-based carbene as a reference molecule and substituted one H atom from each CH2 of the benzyl groups in both sides by CH3, NH2, and CF3 to study the thermodynamic and opto-electronic properties of NHCs theoretically. It was observed that the enthalpy (H), Gibb’s free energy (G), specific heat capacity (C v), and entropy (S) increase significantly in the presence of the electron-withdraw

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2

Mokfi, Moloud, Jörg Rust, Christian W. Lehmann, and Fabian Mohr. "Facile N9-Alkylation of Xanthine Derivatives and Their Use as Precursors for N-Heterocyclic Carbene Complexes." Molecules 26, no. 12 (2021): 3705. http://dx.doi.org/10.3390/molecules26123705.

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The xanthine-derivatives 1,3,7-trimethylxanthine, 1,3-dimethyl-7-benzylxanthine and 1,3-dimethyl-7-(4-chlorobenzyl)xanthine are readily ethylated at N9 using the cheap alkylating agents ethyl tosylate or diethyl sulfate. The resulting xanthinium tosylate or ethyl sulfate salts can be converted into the corresponding PF6- and chloride salts. The reaction of these xanthinium salts with silver(I) oxide results in the formation of different silver(I) carbene-complexes. In the presence of ammonia, ammine complexes [Ag(NHC)(NH3)]PF6 are formed, whilst with Et2NH, the bis(carbene) salts [Ag(NHC)2]PF6

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3

Longevial, Jean-François, Mamadou Lo, Aurélien Lebrun, Danielle Laurencin, Sébastien Clément, and Sébastien Richeter. "Molecular complexes and main-chain organometallic polymers based on Janus bis(carbenes) fused to metalloporphyrins." Dalton Transactions 49, no. 21 (2020): 7005–14. http://dx.doi.org/10.1039/d0dt00594k.

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Janus bis(N-heterocyclic carbenes) composed of a porphyrin core with two N-heterocyclic carbene (NHC) heads fused to opposite pyrroles were used as bridging ligands for the preparation of metal complexes.

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4

Jutand, Anny, Julien Pytkowicz, Sylvain Roland, and Pierre Mangeney. "Mechanism of the oxidative addition of aryl halides to bis-carbene palladium(0) complexes." Pure and Applied Chemistry 82, no. 7 (2010): 1393–402. http://dx.doi.org/10.1351/pac-con-09-09-22.

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Bis-N-heterocyclic carbenes Pd0 complexes, Pd0(NHC)2, are efficient catalysts in Heck reactions performed with aryl bromides or chlorides. The Pd0(NHC)2 that are not stable are generated in situ from PdII precursors PdY2(NHC)2 (Y = halides) after a chemical reduction. The latter procedure can be mimicked by an electrochemical reduction. The transient Pd0(NHCBn)2 is generated by electrochemical reduction of PdY2(NHCBn)2, and its reactivity in oxidative addition to aryl bromides and chlorides is characterized by the same electrochemical technique with the determination of the rate constants. Pd0

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5

Elvan, Üstün, and Şahin Neslihan. "Molecular docking analysis of N-heterocyclic carbene and silver N-heterocyclic carbene complexes with thioredoxin reductas." Journal of Indian Chemical Society Vol. 97, No. 10c, Oct 2020 (2020): 2013–16. https://doi.org/10.5281/zenodo.5970121.

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Department of Chemistry, Faculty of Art and Science, Ordu University, 52200 Ordu, Turkey Department of Basic Education, Faculty of Education, Cumhuriyet University, 58140 Sivas, Turkey <em>E-mail</em>: elvanustun@odu.edu.tr <em>Manuscript received online 20 October 2020, revised and accepted 31 October 2020</em> Molecular docking is a frequently used method in computer-supported drug design studies. It is possible to obtain useful information about the magnitude and character of the interaction between known targets and bioactive molecules thanks to docking methods. Besides the well-known anti

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6

Nonnenmacher, Michael, Dominik M. Buck, and Doris Kunz. "Experimental and theoretical investigations on the high-electron donor character of pyrido-annelated N-heterocyclic carbenes." Beilstein Journal of Organic Chemistry 12 (August 23, 2016): 1884–96. http://dx.doi.org/10.3762/bjoc.12.178.

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Rh(CO)2Cl(NHC) complexes of dipyrido-annelated N-heterocyclic carbenes were prepared. From the C–H coupling constant of the respective imidazolium salts and the N–C–N angle of the N-heterocyclic carbene (NHC), a weaker σ-donor character than that of typical unsaturated NHCs is expected. However, the IR stretching frequencies of their Rh(CO)2Cl complexes suggest an electron-donor character even stronger than that of saturated NHCs. We ascribe this to the extremely weak π-acceptor character of the dipyrido-annelated NHCs caused by the conjugated 14 πe− system that thus allows for an enhanced Rh–

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7

Qie, Boyu, Ziyi Wang, Jingwei Jiang, et al. "Synthesis and characterization of low-dimensional N-heterocyclic carbene lattices." Science 384, no. 6698 (2024): 895–901. http://dx.doi.org/10.1126/science.adm9814.

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The covalent interaction of N-heterocyclic carbenes (NHCs) with transition metal atoms gives rise to distinctive frontier molecular orbitals (FMOs). These emergent electronic states have spurred the widespread adoption of NHC ligands in chemical catalysis and functional materials. Although formation of carbene-metal complexes in self-assembled monolayers on surfaces has been explored, design and electronic structure characterization of extended low-dimensional NHC-metal lattices remains elusive. Here we demonstrate a modular approach to engineering one-dimensional (1D) metal-organic chains and

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8

Ojha, Minita, Shweta Choudhary, and Raj K. Bansal. "3-Benzylbenzothiazolylidene Carbene Catalyzed Isomerization of Dimethyl Maleate to Dimethyl Fumarate: Experimental and Theoretical Results." Current Organocatalysis 7, no. 2 (2020): 108–17. http://dx.doi.org/10.2174/2213337206666191018111354.

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Background: N-Heterocyclic Carbenes (NHCs) have emerged as ubiquitous species having applications in a broad range of fields, including organocatalysis and organometallic chemistry. Since Arduengo and co-workers first isolated a bottlable NHC, namely imidazol-2-ylidene derivative, these nucleophilic species have attained a prominent place in synthetic organic chemistry. The NHC-induced non-asymmetric catalysis has turned out to be a really fruitful area of research in recent years. Methods and Results: The quantitative aspects of the experimental and theoretical investigation of isomerization

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9

Zhu, Tingshun, Ke Xu, and Ziyuan Wang. "N-Heterocyclic Carbene-Organocatalyzed Arene Formation: Application in Atroposelective Synthesis of Polysubstituted Benzenes." Synlett 31, no. 10 (2020): 925–32. http://dx.doi.org/10.1055/s-0039-1690814.

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In recent decades, organocatalysis by N-heterocyclic carbenes (NHCs) has emerged as a versatile and powerful method in organic synthesis. As a result of the power of NHC organocatalysis to produce cyclic compounds, polysubstituted benzenes, which are among the most important cyclic compounds in organic chemistry, can be synthesized efficiently and selectively. This article briefly summarizes the history of NHC organocatalysis, including recent developments in benzene-formation methods, and highlights our recent work in atroposelective arene formation by carbene-catalyzed formal [4+2] cycloadd

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10

Rey, Yannick P., and Ryan Gilmour. "Modulating NHC catalysis with fluorine." Beilstein Journal of Organic Chemistry 9 (December 6, 2013): 2812–20. http://dx.doi.org/10.3762/bjoc.9.316.

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Fluorination often confers a range of advantages in modulating the conformation and reactivity of small molecule organocatalysts. By strategically introducing fluorine substituents, as part of a β-fluoroamine motif, in a triazolium pre-catalyst, it was possible to modulate the behaviour of the corresponding N-heterocyclic carbene (NHC) with minimal steric alterations to the catalyst core. In this study, the effect of hydrogen to fluorine substitution was evaluated as part of a molecular editing study. X-ray crystallographic analyses of a number of derivatives are presented and the conformation

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11

Tang, Xiang-Ting, Fan Yang, Ting-Ting Zhang, et al. "Recent Progress in N-Heterocyclic Carbene Gold-Catalyzed Reactions of Alkynes Involving Oxidation/Amination/Cycloaddition." Catalysts 10, no. 3 (2020): 350. http://dx.doi.org/10.3390/catal10030350.

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Recent rapid development in homogeneous gold catalysis affords an alternative and particularly thriving strategy for the generation of gold carbenes through gold-catalyzed oxidation/amination/cycloaddition of alkynes, while it avoids the employment of hazardous and potentially explosive diazo compounds as starting materials for carbene generation. In addition to facile and secure operation, gold carbenes generated in this strategy display good chemoselectivity distinct from other metal carbenes produced from the related diazo approach. N-heterocyclic carbene (NHC) gold is a special metal compl

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12

Buchspies, Jonathan, Md Mahbubur Rahman, and Michal Szostak. "Suzuki–Miyaura Cross-Coupling of Amides Using Well-Defined, Air- and Moisture-Stable Nickel/NHC (NHC = N-Heterocyclic Carbene) Complexes." Catalysts 10, no. 4 (2020): 372. http://dx.doi.org/10.3390/catal10040372.

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In this Special Issue on N-Heterocyclic Carbenes and Their Complexes in Catalysis, we report the first example of Suzuki–Miyaura cross-coupling of amides catalyzed by well-defined, air- and moisture-stable nickel/NHC (NHC = N-heterocyclic carbene) complexes. The selective amide bond N–C(O) activation is achieved by half-sandwich, cyclopentadienyl [CpNi(NHC)Cl] complexes. The following order of reactivity of NHC ligands has been found: IPr > IMes > IPaul ≈ IPr*. Both the neutral and the cationic complexes are efficient catalysts for the Suzuki–Miyaura cross-coupling of amides. Kinetic stu

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13

Lin, Ivan JB, and Chandra Sekhar Vasam. "Review of gold(I) N-heterocyclic carbenes." Canadian Journal of Chemistry 83, no. 6-7 (2005): 812–25. http://dx.doi.org/10.1139/v05-087.

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This review presents an overview of the work on Au(I)NHC chemistry. The efficiency of different synthetic strategies of Au(I)NHCs is discussed. Transmetallation of Ag(I)NHCs appears to be an easy method as compared with the others. The influence of aurophilicity "a traditional property of a Au(I) center" in making the supramolecular assemblies is also covered. The combination of the Au(I) center with NHCs has great potential in the fields of medicine, catalysis, liquid crystal, and optoelectronic.Key words: goldcarbenes, silvercarbenes, carbene transfer, aurophilicity.

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14

Liu, Ming, Jan C. Namyslo, Martin Nieger, Mika Polamo, and Andreas Schmidt. "From betaines to anionic N-heterocyclic carbenes. Borane, gold, rhodium, and nickel complexes starting from an imidazoliumphenolate and its carbene tautomer." Beilstein Journal of Organic Chemistry 12 (December 8, 2016): 2673–81. http://dx.doi.org/10.3762/bjoc.12.264.

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The mesomeric betaine imidazolium-1-ylphenolate forms a borane adduct with tris(pentafluorophenyl)borane by coordination with the phenolate oxygen, whereas its NHC tautomer 1-(2-phenol)imidazol-2-ylidene reacts with (triphenylphosphine)gold(I) chloride to give the cationic NHC complex [Au(NHC)2][Cl] by coordination with the carbene carbon atom. The anionic N-heterocyclic carbene 1-(2-phenolate)imidazol-2-ylidene gives the complexes [K][Au(NHC−)2], [Rh(NHC−)3] and [Ni(NHC−)2], respectively. Results of four single crystal analyses are presented.

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15

Ellul, Charles E., John P. Lowe, Mary F. Mahon, Paul R. Raithby, and Michael K. Whittlesey. "[Ru3(6-NHC)(CO)10]: synthesis, characterisation and reactivity of rare 46-electron tri-ruthenium clusters." Dalton Transactions 47, no. 13 (2018): 4518–23. http://dx.doi.org/10.1039/c8dt00189h.

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The room temperature reaction of 6-membered ring N-heterocyclic carbenes with [Ru<sub>3</sub>(CO)<sub>12</sub>] affords [Ru<sub>3</sub>(6-NHC)(CO)<sub>10</sub>], rare examples of coordinatively unsaturated, 46-electron tri-ruthenium clusters. Upon mild heating in the presence of C<sub>5</sub>H<sub>5</sub>N, H<sub>2</sub> or PPh<sub>3</sub>, these compounds lose carbene.

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16

McQueen, Caitlin M. A., Anthony F. Hill, Chenxi Ma, and Jas S. Ward. "Ruthenium and osmium complexes of dihydroperimidine-based N-heterocyclic carbene pincer ligands." Dalton Transactions 44, no. 47 (2015): 20376–85. http://dx.doi.org/10.1039/c5dt03728j.

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Double geminal aminal C–H activation processes of the dihydroperimidine based NHC pincer pro-ligands H<sub>2</sub>C(NCH<sub>2</sub>PR<sub>2</sub>)<sub>2</sub>C<sub>10</sub>H<sub>6</sub> are described leading to dihydroperimidinylidene complexes including the first osmium examples.

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17

Beig, Nosheen, Varsha Goyal, and Raj Kumar Bansal. "Application of N-heterocyclic carbene–Cu(I) complexes as catalysts in organic synthesis: a review." Beilstein Journal of Organic Chemistry 19 (September 20, 2023): 1408–42. http://dx.doi.org/10.3762/bjoc.19.102.

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N-Heterocyclic carbenes (NHCs) are a special type of carbenes in which the carbene carbon atom is part of the nitrogen heterocyclic ring. Due to the simplicity of their synthesis and the modularity of their stereoelectronic properties, NHCs have unquestionably emerged as one of the most fascinating and well-known species in chemical science. The remarkable stability of NHCs can be attributed to both kinetic as well as thermodynamic effects caused by its structural features. NHCs constitute a well-established class of new ligands in organometallic chemistry. Although initially NHCs were regarde

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18

Quy, Phan Tu, Nguyen Thi Thanh Hai, Tran Thi Ai My, et al. "A theoretical study on inhibitability of silver(I) N‐heterocyclic carbene and dimer silver(I) N‐heterocyclic carbene complexes against Phytophthora capsici and Fusarium sporotrichioides in Piper nigrum L." Vietnam Journal of Chemistry 59, no. 3 (2021): 405–15. http://dx.doi.org/10.1002/vjch.202000163.

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AbstractPiper nigrum L. (black pepper) is highly susceptible to many infectious diseases, especially foot rot caused by Phytophthora capsici and yellow disease caused by Fusarium sporotrichioides. The inhibitability of silver‐carbene Ag‐NHC and di‐silver‐carbene Di‐Ag‐NHC complexes on protein 6KD3 in Phytophthora capsici and protein 1JFA in Fusarium sporotrichioides was theoretically investigated using molecular docking simulation. The results reveal that both Ag‐NHC and Di‐Ag‐NHC performing strong inhibitory effects towards both proteins. Docking score energy values regarding [Ag‐NHC]‐6KD3 an

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19

Rupar, Paul A., Michael C. Jennings, and Kim M. Baines. "The reactivity of an anionic gallium N-heterocyclic carbene analogue with a solution stable digermene." Canadian Journal of Chemistry 85, no. 2 (2007): 141–47. http://dx.doi.org/10.1139/v07-002.

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The reaction of the anionic gallium(I) N-heterocyclic carbene (NHC) analogue 3 with the solution stable digermene 5 results in the formation of the gallium NHC – germylene complex 8. The gallium NHC – germylene complex 8 was derivatized with CH3I and (CH3)3SiCl.Key words: digermene, carbene analogue, germylene, gallium(I).

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20

Beig, Nosheen, Varsha Goyal, Raakhi Gupta, and Raj K. Bansal. "N-Heterocyclic Carbenes–CuI Complexes as Catalysts: A Theoretical Insight." Australian Journal of Chemistry 74, no. 7 (2021): 503. http://dx.doi.org/10.1071/ch20332.

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The electronic structures of N-heterocyclic carbenes (NHC) imidazolinylidene, thiazolinylidene, imidazolylidene, thiazolylidene, and 1,2,4-triazolylidene and their complexes with cuprous halides (CuX, X=Cl, Br, I) were investigated theoretically at the B3LYP/def2-SVP level. In contrast to other NHCs, imidazolylidene and 1,2,4-triazolylidene do not dimerize owing to the negligible coefficient of the vacant p-orbital at the carbene centre in their respective LUMOs. This is further supported by their greater thermodynamic and kinetic stabilities revealed by greater activation free energies and sm

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21

Zhang, Bo, Yu’ai Duan, Xin Zhang, and Shuai Guo. "Uncommon carbene-to-azole ligand rearrangement of N-heterocyclic carbenes in a ruthenium system." Chemical Communications 57, no. 56 (2021): 6879–82. http://dx.doi.org/10.1039/d1cc01871j.

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22

Sun, Hongsui, Xiao-Yan Yu, Paolo Marcazzan, Brian O. Patrick, and Brian R. James. "Rhodium(I)–(N-heterocyclic carbene)–diphosphine complexes." Canadian Journal of Chemistry 87, no. 9 (2009): 1248–54. http://dx.doi.org/10.1139/v09-118.

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Reactions of [RhCl(COE)(IPr)]2 (1) and [RhCl(COE)(IMes)]2 (2) (COE = cyclooctene; IPr = N,N′-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene; IMes = N,N′-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene) with the diphosphines Ph2P(CH2)nPPh2 and 1,2-bis(diphenylphosphino)benzene (dppbz) give the N-heterocyclic carbene (NHC) – diphosphine – rhodium(I) complexes: RhCl(NHC)[Ph2P(CH2)nPPh2] [NHC = IPr, n = 1 (3); NHC = IMes, n = 1 (4); NHC = IPr, n = 2 (5); NHC = IMes, n = 2 (6); NHC = IPr, n = 4 (7); NHC = IMes, n = 4 (8)] and RhCl(NHC)(dppbz) [NHC = IPr (9); NHC = IMes (10)]. All the complexes are c

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23

Vanden Broeck, Sofie M. P., Fady Nahra, and Catherine S. J. Cazin. "Bulky-Yet-Flexible Carbene Ligands and Their Use in Palladium Cross-Coupling." Inorganics 7, no. 6 (2019): 78. http://dx.doi.org/10.3390/inorganics7060078.

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In recent years, several classes of new N-heterocyclic carbene (NHC) ligands were developed around the concept of “flexible steric bulk”. The steric hindrance of these ligands brings stability to the active species, while ligand flexibility still allows for the approach of the substrate. In this review, the synthesis of several types of new classes, such as IBiox, cyclic alkyl amino carbenes (CAAC), ITent, and IPr* are discussed, as well as how they move the state-of-the-art in palladium catalyzed cross-coupling forward.

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24

Ho, Peter C., Hilary A. Jenkins, James F. Britten, and Ignacio Vargas-Baca. "Building new discrete supramolecular assemblies through the interaction of iso-tellurazole N-oxides with Lewis acids and bases." Faraday Discussions 203 (2017): 187–99. http://dx.doi.org/10.1039/c7fd00075h.

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The supramolecular macrocycles spontaneously assembled by iso-tellurazole N-oxides are stable towards Lewis bases as strong as N-heterocyclic carbenes (NHC) but readily react with Lewis acids such as BR<sub>3</sub> (R = Ph, F). The electron acceptor ability of the tellurium atom is greatly enhanced in the resulting O-bonded adducts, which consequently enables binding to a variety of Lewis bases that includes acetonitrile, 4-dimethylaminopyridine, 4,4′-bipyridine, triphenyl phosphine, a N-heterocyclic carbene and a second molecule of iso-tellurazole N-oxide.

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25

Bysewski, Oliver, Andreas Winter, Phil Liebing, and Ulrich S. Schubert. "Noble Metal Complexes of a Bis-Caffeine Containing NHC Ligand." Molecules 27, no. 13 (2022): 4316. http://dx.doi.org/10.3390/molecules27134316.

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N-Heterocyclic carbenes (NHCs) have seen more and more use over the years. The go-to systems that are usually considered are derivatives of benzimidazole or imidazole. Caffeine possesses an imidazole unit and was already utilized as a carbene-type ligand; however, its use within a tridentate bis-NHC system has—to the best of our knowledge—not been reported so far. The synthesis of the ligand is straightforward and metal complexes are readily available via silver-salt metathesis. A platinum(II) and a palladium(II) complex were isolated and a crystal structure of the former was examined. For the

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26

Tialiou, Alexia, Jiamin Chin, Bernhard K. Keppler, and Michael R. Reithofer. "Current Developments of N-Heterocyclic Carbene Au(I)/Au(III) Complexes toward Cancer Treatment." Biomedicines 10, no. 6 (2022): 1417. http://dx.doi.org/10.3390/biomedicines10061417.

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Since their first discovery, N-heterocyclic carbenes have had a significant impact on organometallic chemistry. Due to their nature as strong σ-donor and π-acceptor ligands, they are exceptionally well suited to stabilize Au(I) and Au(III) complexes in biological environments. Over the last decade, the development of rationally designed NHCAu(I/III) complexes to specifically target DNA has led to a new “gold rush” in bioinorganic chemistry. This review aims to summarize the latest advances of NHCAu(I/III) complexes that are able to interact with DNA. Furthermore, the latest advancements on acy

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27

Prencipe, Filippo, Anna Zanfardino, Michela Di Napoli, et al. "Silver (I) N-Heterocyclic Carbene Complexes: A Winning and Broad Spectrum of Antimicrobial Properties." International Journal of Molecular Sciences 22, no. 5 (2021): 2497. http://dx.doi.org/10.3390/ijms22052497.

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The evolution of antibacterial resistance has arisen as the main downside in fighting bacterial infections pushing researchers to develop novel, more potent and multimodal alternative drugs.Silver and its complexes have long been used as antimicrobial agents in medicine due to the lack of silver resistance and the effectiveness at low concentration as well as to their low toxicities compared to the most commonly used antibiotics. N-Heterocyclic Carbenes (NHCs) have been extensively employed to coordinate transition metals mainly for catalytic chemistry. However, more recently, NHC ligands have

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28

Hock, Andreas, Luis Werner, Christian Luz, and Udo Radius. "N-Heterocyclic carbene and cyclic (alkyl)(amino)carbene adducts of gallium hydrides, gallium chlorides and gallium hydrochlorides." Dalton Transactions 49, no. 32 (2020): 11108–19. http://dx.doi.org/10.1039/d0dt02070b.

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A detailed study on the synthesis and characterization of NHC gallane adducts (NHC)·GaH<sub>3</sub>, (NHC)·GaH<sub>2</sub>Cl, and (NHC)·GaHCl<sub>2</sub> and the reactivity of these adducts with the cyclic (alkyl)(amino)carbene cAAC<sup>Me</sup> is presented.

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29

Fontes, F. A. O., K. K. P. Gomes, Francisca de Fatima P. Medeiros, C. P. Souza, J. F. Sousa, and Uilame Umbelino Gomes. "Synthesis of Niobium Carbide from Ammonium Niobium (V) Oxalate Precursor at Low Temperature in Rotating Cylinder Reactor." Materials Science Forum 498-499 (November 2005): 747–0. http://dx.doi.org/10.4028/www.scientific.net/msf.498-499.747.

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The reaction of oxalic precursor {(NH4)3[NbO(C2O4)3]H2O}, was prepared from the Nb2O5, to niobium carbide (NbC) were performed in a rotating cylinder reactor scale-lab designed to niobium carbide powders synthesis at low temperature (1173 K). The NbC was prepared by a oxalic precursor and as well of commercial niobium pentoxide under flowing CH4- H2 mixtures. The reactor was heated through a bi-partied electric furnace with programmable temperature. The reaction overall time was determined from the curve of methane absorption evolution by gas chromatograph (FID) analysis. The preliminary resul

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30

Zhang, Dongxiang, Jie Li, Xiao Dong, Xing Zhou, Zhi Yang, and Herbert W. Roesky. "N-Heterocyclic Carbene-facilated Condensation of 3-Methylphenylboronic Acid to the Boroxine." Zeitschrift für Naturforschung B 68, no. 5-6 (2013): 453–57. http://dx.doi.org/10.5560/znb.2013-2342.

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The adduct of (3-MeC6H4)3B3O3 with an N-heterocyclic carbene (NHC=1,3-diethyl-4,5- dimethylimidazol-2-ylidene) was prepared by reacting 2.5 equiv. of 3-methylphenylboronic acid with 1 equiv. of the NHC. This reaction shows a novel carbene-facilitated condensation of substituted phenylboronic acid monomers. The structure of the compound (3-MeC6H4)3B3O3(NHC) (1) has been characterized by 1H NMR spectroscopy, elemental analysis, and single-crystal X-ray diffraction studies

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31

Haslinger, S., A. C. Lindhorst, J. W. Kück, M. Cokoja, A. Pöthig, and F. E. Kühn. "Isocyanide substitution reactions at the trans labile sites of an iron(ii) N-heterocyclic carbene complex." RSC Advances 5, no. 104 (2015): 85486–93. http://dx.doi.org/10.1039/c5ra18270k.

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A variety of isocyanide-substituted Fe(ii) N-heterocyclic carbene (NHC) complexes has been synthesized, starting from an Fe(ii) NHC complex with an equatorial, tetradentate bis(pyridyl-NHC) ligand (NCCN).

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32

Wang, Yu-Ting, Bin-Bin Gao, Fan Wang, et al. "Palladium(ii) and palladium(ii)–silver(i) complexes with N-heterocyclic carbene and zwitterionic thiolate mixed ligands: synthesis, structural characterization and catalytic properties." Dalton Transactions 46, no. 6 (2017): 1832–39. http://dx.doi.org/10.1039/c6dt04599e.

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33

Crochet, Pascale, and Victorio Cadierno. "Gold Complexes with Hydrophilic N-Heterocyclic Carbene Ligands and Their Contribution to Aqueous-Phase Catalysis." Catalysts 13, no. 2 (2023): 436. http://dx.doi.org/10.3390/catal13020436.

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N-Heterocyclic carbenes (NHCs) are nowadays one of the most widely employed ligands in organometallic chemistry and homogeneous catalysis due to the inherent stability of the metal-carbene bond and the ease of modification of the backbone as well as the N-wingtips substituents of these ligands. The functionalization of NHCs with hydrophilic groups offers the possibility of using NHC-metal complexes in aqueous catalysis, a hot topic within the Green Chemistry context due to the positive implications associated with the use of water as a reaction medium. In line with the enormous interest arouse

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34

Azpíroz, Ramón, Mert Olgun Karataş, Vincenzo Passarelli, Ismail Özdemir, Jesús J. Pérez-Torrente, and Ricardo Castarlenas. "Preparation of Mixed Bis-N-Heterocyclic Carbene Rhodium(I) Complexes." Molecules 27, no. 20 (2022): 7002. http://dx.doi.org/10.3390/molecules27207002.

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A series of mixed bis-NHC rhodium(I) complexes of type RhCl(η2-olefin)(NHC)(NHC’) have been synthesized by a stepwise reaction of [Rh(μ-Cl)(η2-olefin)2]2 with two different NHCs (NHC = N-heterocyclic carbene), in which the steric hindrance of both NHC ligands and the η2-olefin is critical. Similarly, new mixed coumarin-functionalized bis-NHC rhodium complexes have been prepared by a reaction of mono NHC complexes of type RhCl(NHC-coumarin)(η2,η2-cod) with the corresponding azolium salt in the presence of an external base. Both synthetic procedures proceed selectively and allow the preparation

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35

Jacobsen, Heiko, Andrea Correa, Albert Poater, Chiara Costabile, and Luigi Cavallo. "Understanding the M(NHC) (NHC=N-heterocyclic carbene) bond." Coordination Chemistry Reviews 253, no. 5-6 (2009): 687–703. http://dx.doi.org/10.1016/j.ccr.2008.06.006.

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36

Suduwella, Thilini Malsha, Vikram Singh, Mark Aloisio, et al. "Electrochemical Deposition of N-Heterocyclic Carbene on Steels As a Corrosion Protective Layer." ECS Meeting Abstracts MA2023-02, no. 13 (2023): 1133. http://dx.doi.org/10.1149/ma2023-02131133mtgabs.

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Steels play a vital role in every aspect of day-to-day life. They are major components in construction, transportation, medicine, and etc. Despite their larger usability, steels are suffering from inevitable corrosion. Hence, finding a sustainable solution for corrosion has been a hot topic in the research field for centuries. One extensively studied strategy is applying a protective layer on top of metals. The recent findings show that N-heterocyclic carbene (NHC) has the potency to form a carbon-metal bond through self-assembling1 or electrochemical deposition2 on different metals such as Au

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37

Boubakri, L., S. Yasar, V. Dorcet, et al. "Synthesis and catalytic applications of palladium N-heterocyclic carbene complexes as efficient pre-catalysts for Suzuki–Miyaura and Sonogashira coupling reactions." New Journal of Chemistry 41, no. 12 (2017): 5105–13. http://dx.doi.org/10.1039/c7nj00488e.

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A new palladium complex series with N-heterocyclic carbene (NHC), pyridine and phosphine ligands, PdCl<sub>2</sub>(L)NHC (2a–c)(L = NHC), PdCl<sub>2</sub>(L<sup>1</sup>)NHC(3a–c)(L<sup>1</sup> = pyridine), PdCl<sub>2</sub>(L<sup>2</sup>)NHC(4a–c)(L<sup>2</sup> = triphenylphosphine) was synthesised and fully characterized.

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38

Köppe, R., and H. Schnöckel. "The boron–boron triple bond? A thermodynamic and force field based interpretation of the N-heterocyclic carbene (NHC) stabilization procedure." Chemical Science 6, no. 2 (2015): 1199–205. http://dx.doi.org/10.1039/c4sc02997f.

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From thermodynamic and force constant discussion a new description of bonding of B<sub>2</sub>(NHC)<sub>2</sub> (NHC = N-heterocyclic carbene C<sub>3</sub>N<sub>2</sub>H<sub>2</sub>(C<sub>6</sub>H<sub>3</sub>Pr<sup>i</sup><sub>2</sub>-2,6)<sub>2</sub>) as NHCBBNHC rather than NHC→BB←NHC is given.

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Zhang, Guowen, Man Chao, Shuting Wang, et al. "Synthesis and Catalytic Activity of Chiral Dicarbene Dipalladium Complexes Incorporating the S-binaphthol Unit." Journal of Chemical Research 42, no. 1 (2018): 54–56. http://dx.doi.org/10.3184/174751918x15168768395864.

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A series of chiral di-N-heterocyclic carbene (NHC) dipalladium complexes, [{PdPyCl2}2(di-NHC)], in which di-NHC represents a di-imidazolylidene, featuring an (S)-3,3′-dimethyl-2,2′-dimethoxy-1,1′-binaphthalene spacer between the carbene units, have been prepared. The influence of ligand size on the catalytic activity of these complexes in the Suzuki reaction of phenylboronic acid with p-bromotoluene has been investigated. The most sterically hindered complex, bearing the di-isopropylphenyl group, showed the greatest catalytic activity, and it is active for various aryl halides with different e

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Kelemen, Z., R. Streubel, and L. Nyulászi. "Zwitterionic carbene adducts and their carbene isomers." RSC Advances 5, no. 52 (2015): 41795–802. http://dx.doi.org/10.1039/c5ra07039b.

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41

Jahnke, Mareike C., Tania Pape, and F. Ekkehardt Hahn. "Ligand Exchange at a Gold(I) Carbene Complex." Zeitschrift für Naturforschung B 68, no. 5-6 (2013): 467–73. http://dx.doi.org/10.5560/znb.2013-3076.

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Gold complex [AuCl(NHC)] (NHC=N,N0-dipropylbenzimidazolin-2-ylidene) 1 undergoes facile substitution reactions at the gold(I) center. Treatment of 1 with anionic phenylacetylide or thiophenolate led to the neutral gold complexes 2 and 3, respectively. The cationic gold complexes [Au(NHC)(pyridine)](BF4) [4]BF4 and [Au2(NHC)2(4,4'-bipyridine)](BF4)2 [5](BF4)2 were obtained via abstraction of the chloro ligand from 1 and reaction with the appropriate amine. Reaction of 1 with AgBF4 in the presence of PPh3 instead of an amine led to an inseparable product mixture of the mixed NHC=PPh3 complex [6]

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Roy, Matthew M. D., Michael J. Ferguson, Robert McDonald, and Eric Rivard. "Approaching monocoordination at a silver(i) cation." Chemical Communications 54, no. 5 (2018): 483–86. http://dx.doi.org/10.1039/c7cc08418h.

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Dhara, Debabrata, Pankaj Kalita, Subhadip Mondal, et al. "Reactivity enhancement of a diphosphene by reversible N-heterocyclic carbene coordination." Chemical Science 9, no. 18 (2018): 4235–43. http://dx.doi.org/10.1039/c8sc00348c.

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Duan, Yulian, Tao Wang, Qingxiao Xie, et al. "Highly efficient nitrogen chelated ruthenium carbene metathesis catalysts." Dalton Transactions 45, no. 48 (2016): 19441–48. http://dx.doi.org/10.1039/c6dt03899a.

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45

Lewis-Alleyne, Lesley C., Bassem S. Bassil, Tobias Böttcher, and Gerd-Volker Röschenthaler. "Selective synthesis of cis- and trans-[(NHCMe)2PtCl2] and [NHCMePt(cod)Cl][NHCMePtCl3] using NHCMeSiCl4." Dalton Trans. 43, no. 42 (2014): 15700–15703. http://dx.doi.org/10.1039/c4dt02214a.

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NHC<sup>Me</sup>SiCl<sub>4</sub> was used to selectively synthesise cis and trans-[(NHC<sup>Me</sup>)<sub>2</sub>PtCl<sub>2</sub>], as well as [NHC<sup>Me</sup>Pt(cod)Cl][NHC<sup>Me</sup>PtCl<sub>3</sub>], which revealed the first ever N-heterocyclic carbene analogue of the Cossa's salt anion.

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46

Leitão, Maria Inês P. S., Giulia Francescato, Clara S. B. Gomes, and Ana Petronilho. "Synthesis of Platinum(II) N-Heterocyclic Carbenes Based on Adenosine." Molecules 26, no. 17 (2021): 5384. http://dx.doi.org/10.3390/molecules26175384.

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Organometallic derivatization of nucleosides is a highly promising strategy for the improvement of the therapeutic profile of nucleosides. Herein, a methodology for the synthesis of metalated adenosine with a deprotected ribose moiety is described. Platinum(II) N-heterocyclic carbene complexes based on adenosine were synthesized, namely N-heterocyclic carbenes bearing a protected and unprotected ribose ring. Reaction of the 8-bromo-2′,3′,5′-tri-O-acetyladenosine with Pt(PPh3)4 by C8−Br oxidative addition yielded complex 1, with a PtII centre bonded to C-8 and an unprotonated N7. Complex 1 reac

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47

Binobaid, Abeer, Kingsley J. Cavell, Mikhail S. Nechaev, and Benson M. Kariuki. "Novel Intramolecular CAryl–S Bond Activation by an Electron Rich, Ring-Expanded-NHC-Rh centre: A Combined Experimental and DFT Study." Australian Journal of Chemistry 64, no. 8 (2011): 1141. http://dx.doi.org/10.1071/ch11243.

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The reaction of (o-MeSPh)-N-functionalized tetrahydropyrimidinium salts with KN(SiMe3)2 and [Rh(COD)Cl]2 in THF leads to the formation of a novel dimeric RhIII bis-carbene complex. The reaction involves the unexpected cleavage/oxidative addition of the aryl-sulfur bond to give dimeric metallated RhIII with bridging MeS< moieties. This unusual reaction is probably a consequence of the sterically imposing structure and strong donor capacity of ring-expanded N-heterocyclic carbenes (RE-NHCs). An X-ray structure of the [(Ph,DIPP-NHC)Rh(Cl)(SMe)2] product complex has been obtained, and DFT studi

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Yang, Longhua, Yanli Yuan, Hongming Wang, Ning Zhang, and Sanguo Hong. "Theoretical insights into copper(i)–NHC-catalyzed C–H carboxylation of terminal alkynes with CO2: the reaction mechanisms and the roles of NHC." RSC Adv. 4, no. 61 (2014): 32457–66. http://dx.doi.org/10.1039/c4ra00254g.

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Bensalah, Donia, Nevin Gurbuz, Ismail Özdemir, Rafik Gatri, Lamjed Mansour, and Naceur Hamdi. "Synthesis, Characterization, Antimicrobial Properties, and Antioxidant Activities of Silver-N-Heterocyclic Carbene Complexes." Bioinorganic Chemistry and Applications 2023 (May 26, 2023): 1–15. http://dx.doi.org/10.1155/2023/3066299.

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The emergence of antimicrobial resistance has become a major handicap in the fight against bacterial infections, prompting researchers to develop new, more effective, and multimodal alternatives. Silver and its complexes have long been used as antimicrobial agents in medicine because of their lack of resistance to silver, their low potency at low concentrations, and their low toxicity compared to most commonly used antibiotics. N-Heterocyclic carbenes (NHCs) are widely used for coordination of transition metals, mainly in catalytic chemistry. In this study, several N-alkylated benzimidazolium

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50

Raed, Anas Abo, Vasudevan Dhayalan, Shahar Barkai, and Anat Milo. "N-Heterocyclic Carbene Triazolium Salts Containing Brominated Aromatic Motifs: Features and Synthetic Protocol." CHIMIA International Journal for Chemistry 74, no. 11 (2020): 878–82. http://dx.doi.org/10.2533/chimia.2020.878.

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In this work, we provide a brief overview of the role of N-aryl substituents on triazolium N-heterocyclic carbene (NHC) catalysis. This synopsis provides context for the disclosed synthetic protocol for new chiral N-heterocyclic carbene (NHC) triazolium salts with brominated aromatic motifs. Incorporating brominated aryl rings into NHC structures is challenging, probably due to the substantial steric and electronic influence these substituents exert throughout the synthetic protocol. However, these exact characteristics make it an interesting N-aryl substituent, because the electronic and ster

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