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Journal articles on the topic 'N-Heterocyclic carbenes complexes'

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Author: Grafiati

Published: 4 June 2021

Last updated: 12 February 2022

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1

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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2

Zhao, Shixian, Feifei Wu, Yuyu Ma, Wanzhi Chen, Miaochang Liu, and Huayue Wu. "Enhancement of N-heterocyclic carbenes on rhodium catalyzed olefination of triazoles." Organic & Biomolecular Chemistry 14, no. 8 (2016): 2550–55. http://dx.doi.org/10.1039/c5ob02397a.

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3

Frański, Rafał, Błażej Gierczyk, Grzegorz Schroeder, Stefan Pieper, Andreas Springer, and Michael Linscheid. "Electrospray ionization mass spectrometric study of mercury complexes of N-heterocyclic carbenes derived from 1,2,4-triazolium salt precursors." Open Chemistry 5, no. 1 (March 1, 2007): 316–29. http://dx.doi.org/10.2478/s11532-006-0050-0.

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AbstractBy mixing 1,2,4-triazolium salts (precursors of N-heterocyclic carbenes 1–6) with mercury acetate, a number of complexes have been obtained under electrospray ionization condition. Carbenes 1 and 2 contain one carbene center; therefore, they are able to bond only one mercury cation. Carbenes 3–5 contain two carbene centers; therefore, they can bond two mercury cations. Mercury complexes of 1–5 always contain an acetate anion attached to a mercury cation. Carbene 6 also contains two carbene centers; however, its structure allows formation of a complex containing mercury bonded simultaneously to both centers, therefore, the complex that does not contain an acetate anion. The MS/MS spectra taken for complexes of carbenes 1–5 have shown formation of a cation corresponding to N1 substituent (adamantyl or benzyl), and those of complexes of carbenes 3–5 (doubly charged ions) have also shown the respective complementary partner ions. Mercury complex of 2 has yielded some other interesting fragmentation pathways, e.g. a loss of the HHgOOCCH3 molecule. The fragmentation pathway of the mercury complexes of 6 was found to be complicated.

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4

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 (September 4, 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 reacted at N7 with HBF4 or methyl iodide, yielding protic carbene 2 or methyl carbene 3, respectively. Deprotection of 1 to yield 4 was achieved with NH4OH. Deprotected compound 4 reacted at N7 with HCl solutions to yield protic NHC 5 or with methyl iodide yielding methyl carbene 6. Protic N-heterocyclic carbene 5 is not stable in DMSO solutions leading to the formation of compound 7, in which a bromide was replaced by chloride. The cis-influence of complexes 1–7 was examined by 31P{1H} and 195Pt NMR. Complexes 2, 3, 5, 6 and 7 induce a decrease of 1JPt,P of more than 300 Hz, as result of the higher cis-influence of the N-heterocyclic carbene when compared to the azolato ligand in 1 and 4.

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5

Wilhelm, René, Eduard Rais, and Ulrich Flörke. "Reactivity of Grubbs–Hoveyda II Complexes Including Extended N-Heterocyclic Carbenes with a Bicyclic Camphor-Based Framework." Synthesis 49, no. 13 (June 7, 2017): 2852–64. http://dx.doi.org/10.1055/s-0036-1588849.

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This feature article discusses the synthesis of new asymmetric Grubbs–Hoveyda II complexes with extended N-heterocyclic carbenes containing a bicyclic camphor-based framework. The new enantiopure complexes can be prepared in a short route from the chiral pool. The extended carbene-based catalyst shows high activity in olefin metathesis reactions. The new complexes exhibited enantioselectivity in an asymmetric ROCM desymmetrization. Depending on the substituents on the nitrogen atoms of the carbenes, the opposite enantiomer was formed in excess.

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6

Michalak and Kośnik. "Chiral N-heterocyclic Carbene Gold Complexes: Synthesis and Applications in Catalysis." Catalysts 9, no. 11 (October 25, 2019): 890. http://dx.doi.org/10.3390/catal9110890.

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N-Heterocyclic carbenes have found many applications in modern metal catalysis, due to the formation of stable metal complexes, and organocatalysis. Among a myriad of N-heterocyclic carbene metal complexes, gold complexes have gained a lot of attention due to their unique propensity for the activation of carbon-carbon multiple bonds, allowing many useful transformations of alkynes, allenes, and alkenes, inaccessible by other metal complexes. The present review summarizes synthetic efforts towards the preparation of chiral N-heterocyclic gold(I) complexes exhibiting C2 and C1 symmetry, as well as their applications in enantioselective catalysis. Finally, the emerging area of rare gold(III) complexes and their preliminary usage in asymmetric catalysis is also presented.

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7

Ho, Luong Phong, Lukas Körner, Thomas Bannenberg, and Matthias Tamm. "Chalcogen complexes of anionic N-heterocyclic carbenes." Dalton Transactions 49, no. 38 (2020): 13207–17. http://dx.doi.org/10.1039/d0dt02392b.

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8

Mas-Marzá, Elena, Patrícia M. Reis, Eduardo Peris, and Beatriz Royo. "Dioxomolybdenum(VI) complexes containing N-heterocyclic carbenes." Journal of Organometallic Chemistry 691, no. 12 (June 2006): 2708–12. http://dx.doi.org/10.1016/j.jorganchem.2006.02.004.

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9

Weskamp, Thomas, Florian J. Kohl, and Wolfgang A. Herrmann. "N-heterocyclic carbenes: novel ruthenium–alkylidene complexes." Journal of Organometallic Chemistry 582, no. 2 (June 1999): 362–65. http://dx.doi.org/10.1016/s0022-328x(99)00163-1.

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10

Herrmann, Wolfgang A., Florian J. Kohl, and Jurgen Schwarz. "ChemInform Abstract: Complexes of N-Heterocyclic Carbenes." ChemInform 32, no. 1 (January 2, 2001): no. http://dx.doi.org/10.1002/chin.200101252.

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11

Herrmann, Wolfgang A., Gisela Gerstberger, and Michael Spiegler. "Nickel(II) Complexes of N-Heterocyclic Carbenes†." Organometallics 16, no. 10 (May 1997): 2209–12. http://dx.doi.org/10.1021/om961038g.

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12

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 smaller standard free energies for their dimerization. Second-order perturbation interactions in the natural bond orbital (NBO) analysis of the NHCs indicate that six π electrons are delocalized in imidazolylidene, thiazolylidene, and 1,2,4-triazolylidene, conferring aromatic character and thereby enhancing their thermodynamic stability. NBO analysis reveals the existence of effective back bonding from a d orbital of Cu to the NHC, increasing the Wiberg bond index of the C–Cu bond to ~1.5. Owing to the large electronic chemical potential (μ) and high nucleophilicity indices, NHCs are able to transfer their electron density effectively to the cuprous halides having low μ values and high electrophilicity indices to yield stable NHC–CuI complexes. Large values of the Fukui function f(r) at the carbene centre of the NHCs and Cu atom of the NHC–CuI complexes indicate their softness. Imidazolylidene was found to be the softest, rationalizing wide use of this class of NHCs as ligands. The coordination of the NHCs to cuprous halides is either barrierless or has a very low activation free energy barrier. In the A3 reaction wherein NHC–Cu(I) complexes are used as catalyst, the reaction of NHC–CuI with phenylacetylene changes the latter into acetylide accompanied by raising the energy level of its HOMO considerably compared with the level of the uncomplexed alkyne, making its reaction with benzaldehyde barrierless.

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13

Dash, Chandrakanta, Animesh Das, and H. V. Rasika Dias. "Mercury(II) Complexes of Anionic N-Heterocyclic Carbene Ligands: Steric Effects of the Backbone Substituent." Molecules 25, no. 16 (August 16, 2020): 3741. http://dx.doi.org/10.3390/molecules25163741.

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Mercury(II) complexes (Me-maloNHCDipp)HgCl (1b), (t-Bu-maloNHCDipp)HgCl (2b) and (t-Bu-maloNHCDipp)HgMe (2c) supported by anionic N-heterocyclic carbenes have been obtained in good yields from the reaction of the potassium salt of N-heterocyclic carbene ligand precursors and mercury(II) salts, HgCl2 and MeHgI. These molecules have been characterized by 1H-NMR, 13C-NMR and IR spectroscopy and elemental analysis. X-ray crystal structures of 1b and 2b are also presented. Interestingly, complex 1b is polymeric {(Me-maloNHCDipp)HgCl}n in the solid state, as a result of inter-molecular Hg-O contacts, and features rare three coordinate mercury sites with a T-shaped arrangement, whereas the (t-Bu-maloNHCDipp)HgCl (2b) is monomeric and has a linear, two-coordinate mercury center. The formation of T-shaped structure and the aggregation of complex 1b is attributable to the reduced steric demand of the N-heterocyclic carbene ligand backbone substituent.

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14

Krüger, Anneke, and Martin Albrecht. "Abnormal N-heterocyclic Carbenes: More than Just Exceptionally Strong Donor Ligands." Australian Journal of Chemistry 64, no. 8 (2011): 1113. http://dx.doi.org/10.1071/ch11265.

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Complexes comprising a so-called abnormal carbene ligand, which displays pronounced mesoionic character, have recently been shown to be competent catalyst precursors for bond activation processes and oxidative transformations, including base-free alcohol oxidation and water oxidation. In this highlight we propose that these abnormal carbene ligands are not just useful spectator ligands but also actively participate in the bond activation step. This mode of action is partially based on the exceptionally strong donor properties of the ligand and, specifically, on the mesoionic character of these abnormal carbenes. The mesoionic properties provide a reservoir for charges and holes and thus induce efficient ligand-metal cooperativity, which is beneficial in particular for oxidation catalysis that involves concerted proton and electron transfer processes.

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15

Kückmann, Theresa I., and Ulrich Abram. "Rhenium(V) Oxo Complexes with N-Heterocyclic Carbenes." Inorganic Chemistry 43, no. 22 (November 2004): 7068–74. http://dx.doi.org/10.1021/ic0497578.

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16

Baratta, Walter, Eberhardt Herdtweck, Wolfgang A. Herrmann, Pierluigi Rigo, and Jürgen Schwarz. "New Ruthenium(II) Complexes Bearing N-Heterocyclic Carbenes." Organometallics 21, no. 10 (May 2002): 2101–6. http://dx.doi.org/10.1021/om020053k.

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17

Hashimoto, Takayoshi, Ryoko Hoshino, Tsubasa Hatanaka, Yasuhiro Ohki, and Kazuyuki Tatsumi. "Dinuclear Iron(0) Complexes of N-Heterocyclic Carbenes." Organometallics 33, no. 4 (February 5, 2014): 921–29. http://dx.doi.org/10.1021/om401039z.

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18

Nahra, Fady, Kristof Van Hecke, Alan R. Kennedy, and David J. Nelson. "Coinage metal complexes of selenoureas derived from N-heterocyclic carbenes." Dalton Transactions 47, no. 31 (2018): 10671–84. http://dx.doi.org/10.1039/c8dt01506f.

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19

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–CO backbonding. This extremely low π-acceptor ability is also corroborated by the 77Se NMR chemical shift of −55.8 ppm for the respective selenourea, the lowest value ever measured for imidazole derived selenoureas. DFT-calculations of the free carbene confirm the low σ-donor character by the fact that the σ-orbital of the carbene is the HOMO−1 that lies 0.58 eV below the HOMO which is located at the π-system. Natural population analysis reveals the lowest occupation of the pπ-orbital for the saturated carbene carbon atom and the highest for the pyrido-annelated carbene. Going from the free carbene to the Rh(CO)2Cl(NHC) complexes, the increase in occupancy of the complete π-system of the carbene ligand upon coordination is lowest for the pyrido-annelated carbene and highest for the saturated carbene.

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20

Schwedtmann, Kai, Robin Schoemaker, Felix Hennersdorf, Antonio Bauzá, Antonio Frontera, Robert Weiss, and Jan J. Weigand. "Cationic 5-phosphonio-substituted N-heterocyclic carbenes." Dalton Transactions 45, no. 28 (2016): 11384–96. http://dx.doi.org/10.1039/c6dt01871h.

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Cationic NHCs featuring a phosphonium moiety in the 5-position are prepared from the reaction of imidazolium salts with a tert. phosphane. They are used as ligands for the preparation of transition metal complexes, dehydrogenation reactions of prim. and sec. phosphanes and the preparation of a N-heterocyclic olefin (NHO).

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21

Wang, Yuzhong, Hunter P. Hickox, Pingrong Wei, and Gregory H. Robinson. "C4-Ferrocenylsilyl-bridged and -substituted N-heterocyclic carbenes: complexation of germanium chloride." Dalton Transactions 46, no. 17 (2017): 5508–12. http://dx.doi.org/10.1039/c7dt00066a.

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22

Savka, Roman, Sabine Foro, and Herbert Plenio. "Pentiptycene-based concave NHC–metal complexes." Dalton Transactions 45, no. 27 (2016): 11015–24. http://dx.doi.org/10.1039/c6dt01724j.

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23

Kuehn, Laura, Antonius F. Eichhorn, Todd B. Marder, and Udo Radius. "Copper(I) complexes of N-alkyl-substituted N-Heterocyclic carbenes." Journal of Organometallic Chemistry 881 (February 2019): 25–33. http://dx.doi.org/10.1016/j.jorganchem.2018.11.032.

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24

Hahn, F. Ekkehardt, Beate Heidrich, Thomas Lügger, and Tania Pape. "Pd(II) Complexes of N-Allyl Substituted N-Heterocyclic Carbenes." Zeitschrift für Naturforschung B 59, no. 11-12 (December 1, 2004): 1519–23. http://dx.doi.org/10.1515/znb-2004-11-1223.

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The unsymmetrically substituted imidazolium salt 1-ethyl-3-allyl-imidazolium bromide 1 was synthesized by treatment of imidazole with one equivalent each of n-butyl lithium and ethyl bromide followed by treatment with one equivalent of allyl bromide. The symmetrically substituted derivatives 1,3-diallyl-imidazolium bromide 2 and 1,3-bis(3-methyl-2-butenyl)-imidazolium bromide 3 were obtained from imidazole and two equivalents of allyl bromide or 4-bromo-2-methyl-2-butenyl bromide, respectively, in the presence of sodium hydrogencarbonate as a base. The imidazolium bromides 1- 3 react with Pd(OAc)2 to afford the palladium(II) dicarbene complexes trans-[PdBr2(L)2] (L = 1- ethyl-3-allyl-imidazolin-2-ylidene, 4; L = 1,3-diallyl-imidazolin-2-ylidene, 5; L = 1,3-di(3-methyl-2- butenyl)imidazolin-2-ylidene, 6) by in situ deprotonation of the imidazolium salts. The X-ray structure analyses of 4- 6 show all three complexes to be mononuclear with palladium(II) coordinated in a square-planar fashion by two carbene and two bromo ligands.

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25

Caramori, Giovanni F., Leone C. Garcia, Diego M. Andrada, and Gernot Frenking. "Ruthenium(ii) complexes of N-heterocyclic carbenes derived from imidazolium-linked cyclophanes." Dalton Trans. 43, no. 39 (2014): 14710–19. http://dx.doi.org/10.1039/c4dt01473a.

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26

Martynova, Ekaterina A., Nikolaos V. Tzouras, Gianmarco Pisanò, Catherine S. J. Cazin, and Steven P. Nolan. "The “weak base route” leading to transition metal–N-heterocyclic carbene complexes." Chemical Communications 57, no. 32 (2021): 3836–56. http://dx.doi.org/10.1039/d0cc08149c.

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27

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 (March 31, 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 studies demonstrate that the reactions are complete in < 1 h at 80 °C. Complete selectivity for the cleavage of exocyclic N-acyl bond has been observed under the experimental conditions. Given the utility of nickel catalysis in activating unreactive bonds, we believe that well-defined and bench-stable [CpNi(NHC)Cl] complexes will find broad application in amide bond and related cross-couplings of bench-stable acyl-electrophiles.

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28

Arnold, Polly L., Shaheed A. Mungur, Alexander J. Blake, and Claire Wilson. "Anionic Amido N-Heterocyclic Carbenes: Synthesis of Covalently Tethered Lanthanide–Carbene Complexes." Angewandte Chemie 115, no. 48 (December 15, 2003): 6163–66. http://dx.doi.org/10.1002/ange.200352710.

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29

Arnold, Polly L., Shaheed A. Mungur, Alexander J. Blake, and Claire Wilson. "Anionic Amido N-Heterocyclic Carbenes: Synthesis of Covalently Tethered Lanthanide–Carbene Complexes." Angewandte Chemie International Edition 42, no. 48 (December 15, 2003): 5981–84. http://dx.doi.org/10.1002/anie.200352710.

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30

Iglesias, Manuel, Dirk J. Beetstra, James C. Knight, Li-Ling Ooi, Andreas Stasch, Simon Coles, Louise Male, et al. "Novel Expanded Ring N-Heterocyclic Carbenes: Free Carbenes, Silver Complexes, And Structures." Organometallics 27, no. 13 (July 2008): 3279–89. http://dx.doi.org/10.1021/om800179t.

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31

Jiang, Li, Bodong Zhang, Guillaume Médard, Ari Paavo Seitsonen, Felix Haag, Francesco Allegretti, Joachim Reichert, Bernhard Kuster, Johannes V. Barth, and Anthoula C. Papageorgiou. "N-Heterocyclic carbenes on close-packed coinage metal surfaces: bis-carbene metal adatom bonding scheme of monolayer films on Au, Ag and Cu." Chemical Science 8, no. 12 (2017): 8301–8. http://dx.doi.org/10.1039/c7sc03777e.

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32

Lv, Gaochao, Liubin Guo, Ling Qiu, Hui Yang, Tengfei Wang, Hong Liu, and Jianguo Lin. "Lipophilicity-dependent ruthenium N-heterocyclic carbene complexes as potential anticancer agents." Dalton Transactions 44, no. 16 (2015): 7324–31. http://dx.doi.org/10.1039/c5dt00169b.

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33

Kuchar, Julia, Jörg Rust, Christian W. Lehmann, and Fabian Mohr. "Acylseleno- and acylthioureato complexes of gold(i) N-heterocyclic carbenes." New Journal of Chemistry 43, no. 27 (2019): 10750–54. http://dx.doi.org/10.1039/c9nj02229e.

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34

Henderson, Alexander S., John F. Bower, and M. Carmen Galan. "Carbohydrate-based N-heterocyclic carbenes for enantioselective catalysis." Org. Biomol. Chem. 12, no. 45 (2014): 9180–83. http://dx.doi.org/10.1039/c4ob02056a.

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Versatile syntheses of C2-linked and C₂-symmetric carbohydrate-based NHC·HCls from functionalised amino-carbohydrate derivatives are reported. The corresponding Rh complexes were evaluated in asymmetric hydrosilylation of ketones.

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35

Scattolin, Thomas, Claudio Santo, Nicola Demitri, Luciano Canovese, and Fabiano Visentin. "Chemoselective oxidative addition of vinyl sulfones mediated by palladium complexes bearing picolyl-N-heterocyclic carbene ligands." Dalton Transactions 49, no. 17 (2020): 5684–94. http://dx.doi.org/10.1039/d0dt01144d.

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36

Shanmuganathan, Saravanakumar, Olaf Kühl, Peter Jones, and Joachim Heinicke. "Nickel and palladium complexes of enolatefunctionalised N-heterocyclic carbenes." Open Chemistry 8, no. 5 (October 1, 2010): 992–98. http://dx.doi.org/10.2478/s11532-010-0071-6.

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AbstractThe reaction of chloroethyltrimethylsilylether with 1-methylimidazole furnishes an ionic liquid that undergoes methanolysis to crystalline 2-hydroxyethylimidazolium chloride (crystal structure presented). Conversion to defined hydroxyethylimidazol-2-ylidene nickel complexes failed, but was accomplished with 1-methyl-3-acetophenyl-imidazolium bromide. The bis(NHC⋂O−) nickel(II) chelate is formed, rather than a methallylnickel monochelate, but with nickelocene a monochelate NiCp complex was detected. The bulky 1-(2,6-diisopropylphenyl)-3-(2’-phenyl-enolato)-imidazol-2-ylidene allylpalladium chloride was obtained in pure form. Attempts to generate catalysts for ethylene oligomerization by in situ techniques have failed so far whereas P⋂O− ligands, comparable by the P-C diagonal relationship, provide active catalysts.

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37

Hock, Sebastian J., Lars-Arne Schaper, Wolfgang A. Herrmann, and Fritz E. Kühn. "Group 7 transition metal complexes with N-heterocyclic carbenes." Chemical Society Reviews 42, no. 12 (2013): 5073. http://dx.doi.org/10.1039/c3cs60019j.

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38

Dash, Chandrakanta, Peter Kroll, Muhammed Yousufuddin, and H. V. Rasika Dias. "Isolable, gold carbonyl complexes supported by N-heterocyclic carbenes." Chemical Communications 47, no. 15 (2011): 4478. http://dx.doi.org/10.1039/c1cc10622h.

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39

Douthwaite, Richard E., Daniel Haüssinger, Malcolm L. H. Green, Peter J. Silcock, Pedro T. Gomes, Ana M. Martins, and Andreas A. Danopoulos. "Cationic Nickel(II) Complexes of Chelating N-Heterocyclic Carbenes." Organometallics 18, no. 22 (October 1999): 4584–90. http://dx.doi.org/10.1021/om990398b.

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40

Jahnke, Mareike C., and F. Ekkehardt Hahn. "Complexes Bearing Protic N-Heterocyclic Carbenes: Synthesis and Applications." Chemistry Letters 44, no. 3 (March 5, 2015): 226–37. http://dx.doi.org/10.1246/cl.141052.

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41

Abdur-Rashid, Kamaluddin, Terry Fedorkiw, Alan J. Lough, and Robert H. Morris. "Coordinatively Unsaturated Hydridoruthenium(II) Complexes of N-Heterocyclic Carbenes." Organometallics 23, no. 1 (January 2004): 86–94. http://dx.doi.org/10.1021/om034178g.

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42

Chiou, Josh Y. Z., Shih C. Luo, Wan C. You, Amitabha Bhattacharyya, C. Sekhar Vasam, Cyong H. Huang, and Ivan J. B. Lin. "Gold(I) Complexes of N-Heterocyclic Carbenes and Pyridines." European Journal of Inorganic Chemistry 2009, no. 13 (May 2009): 1950–59. http://dx.doi.org/10.1002/ejic.200801186.

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43

Jin, Hanpeng, Tristan Tsai Yuan Tan, and F. Ekkehardt Hahn. "Synthesis of Complexes with Abnormal “Protic” N-Heterocyclic Carbenes." Angewandte Chemie International Edition 54, no. 46 (September 25, 2015): 13811–15. http://dx.doi.org/10.1002/anie.201507206.

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44

Wang, Guocang, Lisa Pecher, Gernot Frenking, and H. V. Rasika Dias. "Vinyltrifluoroborate Complexes of Silver Supported by N -Heterocyclic Carbenes." European Journal of Inorganic Chemistry 2018, no. 37 (September 25, 2018): 4142–52. http://dx.doi.org/10.1002/ejic.201800899.

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45

Almallah, Hamzé, Mélodie Nos, Virgile Ayzac, Eric Brenner, Dominique Matt, Christophe Gourlaouen, Mohamad Jahjah, and Akram Hijazi. "Complexes featuring N-heterocyclic carbenes with bowl-shaped wingtips." Comptes Rendus Chimie 22, no. 4 (April 2019): 299–309. http://dx.doi.org/10.1016/j.crci.2019.01.008.

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46

Frosch, Jenni, Lukas Körner, Marvin Koneczny, and Matthias Tamm. "Sodium and Potassium Complexes of Anionic N‐Heterocyclic Carbenes." Zeitschrift für anorganische und allgemeine Chemie 647, no. 9 (March 22, 2021): 998–1004. http://dx.doi.org/10.1002/zaac.202100041.

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47

Kiefer, Claude, Sebastian Bestgen, Michael T. Gamer, Sergei Lebedkin, Manfred M. Kappes, and Peter W. Roesky. "Alkynyl-functionalized gold NHC complexes and their coinage metal clusters." Dalton Transactions 44, no. 30 (2015): 13662–70. http://dx.doi.org/10.1039/c5dt02228b.

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Phenylpropynyl-functionalized N-heterocyclic carbenes as ligands for the synthesis of heterometallic hexanuclear coinagemetal clusters which exhibit mixed metallophillic interactions and intense white photoluminescence at low temperature.

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48

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 (June 17, 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 were isolated. Using the xanthinium chloride salts neutral silver(I) carbenes [Ag(NHC)Cl] were prepared. These silver complexes were used in a variety of transmetallation reactions to give the corresponding gold(I), ruthenium(II) as well as rhodium(I) and rhodium(III) complexes. The compounds were characterized by various spectroscopic methods as well as X-ray diffraction.

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49

Espinal-Viguri, Maialen, Victor Varela-Izquierdo, Fedor M. Miloserdov, Ian M. Riddlestone, Mary F. Mahon, and Michael K. Whittlesey. "Correction: Heterobimetallic ruthenium–zinc complexes with bulky N-heterocyclic carbenes: syntheses, structures and reactivity." Dalton Transactions 49, no. 20 (2020): 6896. http://dx.doi.org/10.1039/d0dt90091e.

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Correction for ‘Heterobimetallic ruthenium–zinc complexes with bulky N-heterocyclic carbenes: syntheses, structures and reactivity’ by Maialen Espinal-Viguri et al., Dalton Trans., 2019, 48, 4176–4189, DOI: 10.1039/C8DT05023F.

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Grindell, Richard, Benjamin M. Day, Fu-Sheng Guo, Thomas Pugh, and Richard A. Layfield. "Activation of C–H bonds by rare-earth metallocene-butyl complexes." Chemical Communications 53, no. 72 (2017): 9990–93. http://dx.doi.org/10.1039/c7cc05597h.

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The stable metallocene-butyl complexes [(Cp^Me)₂M(ⁿBu)]₂ (M = Y, Dy) were synthesized and their reactivity towards to ferrocene and bulky N-heterocyclic carbenes investigated.

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