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Journal articles on the topic 'Metal carbene complex'

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Published: 4 June 2021

Last updated: 1 February 2022

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1

Cui, Peng, and Vlad M. Iluc. "Redox-induced umpolung of transition metal carbenes." Chemical Science 6, no. 12 (2015): 7343–54. http://dx.doi.org/10.1039/c5sc02859k.

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An unprecedented umpolung of a nucleophilic palladium carbene complex was realized by successive one-electron oxidations to generate a cationic carbene complex, which shows electrophilic behavior toward nucleophiles resulting from a polarity inversion of the Pd–C_carbene bond.

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2

Fischer, Ernst Otto, Christos Apostolidis, Ernst Dornberger, Alexander C. Filippou, Basil Kanellakopulos, Bernhard Lungwitz, Jakob Müller, Bernhard Powietzka, Jean Rebizant, and Werner Roth. "Carben- und Carbin-Komplexe des Technetiums und Rheniums - Synthese, Struktur und Reaktionen / Carbene and Carbyne Complexes of Technetium and Rhenium - Synthesis, Structure and Reactions." Zeitschrift für Naturforschung B 50, no. 9 (September 1, 1995): 1382–95. http://dx.doi.org/10.1515/znb-1995-0916.

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AbstractSynthesis, structure and reactions of technetium and rhenium complexes bearing metal-carbon multiple bonds are reported. Addition of LiPh to Cp*M (CO)3 (1a : M = Tc; 1b: M = Re) (Cp* = η5-C5Me5) in Et2O yields the acyl complexes Li[Cp*(CO)2MC(O)Ph]·Et2O (2a: M = Tc; 2 b: M = Re). These are converted with Et3OBF4 into the carbene complexes Cp*(CO)2M = C(OEt)Ph (3a, 3b). Reaction of 3a and 3 b with BCl3 affords the carbyne complexes [Cp*(CO)2M ≡ CPh]BCl4 (4a, 4b) in high yield. The acyl complex 2b can be directly converted into the carbyne complex [Cp*(CO)2Re ≡ CPh]Br (5b), when it is treated with oxalyl bromide. Nucleophiles add at the carbynecarbon atoms of 4a and 4b, as demonstrated by the reaction with NaOCy (Cy = cyclohexyl) to afford the carbene complexes Cp*(CO)2M = C(OCy)Ph (6a, 6b). Similarly, reaction of P(OMe)3 with [Cp*(CO)2Re ≡ CPh]Cl (5b'), the latter being generated in situ from 2b and oxalyl chloride, gives the ylide complex {Cp*(CO)2Re = C[P(OMe)3]Ph}Cl (7b'). In comparison, addition of P(OMe)3 to [Cp*(CO)2Tc ≡ CPh]Cl (5a'), generated in situ from 2a and oxalyl chloride, induces a carbvne-carbonvl coupling reaction resulting in the formation of the ketenyl complex . Thermolysis of the compounds 2a, 2b, 4a, 4b and 7b' has been studied in vacuo and the products of decomposition identified by IR spectroscopy. The solid-state structure of the carbene complexes 3 a and 3 b was determined by single crystal X-ray diffraction studies. Both compounds crystallize in the monoclinic space group P21/n with very similar unit cell data. Striking feature of the isostructural carbene complexes is the nearly perpendicular orientation of the carbene ligand relative to the Cp* ring.

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3

Tang, Xiang-Ting, Fan Yang, Ting-Ting Zhang, Yi-Fan Liu, Si-Yu Liu, Tong-Fu Su, Dong-Can Lv, and Wen-Bo Shen. "Recent Progress in N-Heterocyclic Carbene Gold-Catalyzed Reactions of Alkynes Involving Oxidation/Amination/Cycloaddition." Catalysts 10, no. 3 (March 20, 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 complex that can be used as ancillary ligands, which provides enhanced stability and can also act as an efficient chiral directing group. In this review, we will present an overview of these recent advances in alkyne oxidation/amination/cycloaddition by highlighting their specificity and applicability, aiming to facilitate progress in this very exciting area of research.

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4

Jo, Minyoung, Jingbai Li, Alina Dragulescu-Andrasi, Andrey Yu Rogachev, and Michael Shatruk. "Incorporation of coinage metal–NHC complexes into heptaphosphide clusters." Dalton Transactions 49, no. 37 (2020): 12955–59. http://dx.doi.org/10.1039/d0dt03119d.

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A Me₃Si-protected P₇ cage reacts with N-heterocyclic-carbene complexes of coinage metals to yield a mononuclear Cu(i) complex featuring a Cu(η⁴-P₇) core and a trinuclear Au(i) complex with linearly coordinated metal ions attached to the P₇ cluster.

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5

Wang, Ban, Isaac G. Howard, Jackson W. Pope, Eric D. Conte, and Yongming Deng. "Bis(imino)pyridine iron complexes for catalytic carbene transfer reactions." Chemical Science 10, no. 34 (2019): 7958–63. http://dx.doi.org/10.1039/c9sc02189b.

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6

Dötz, K. H., R. Ehlenz, W. Straub, J. C. Weber, K. Airola, and M. Nieger. "Organotransition metal modified sugars 4. Carbene complex functionalized acyclic carbohydrates." Journal of Organometallic Chemistry 548, no. 1 (December 1997): 91–98. http://dx.doi.org/10.1016/s0022-328x(97)00335-5.

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7

Weismann, Julia, Rory Waterman, and Viktoria H. Gessner. "Metal-Ligand Cooperativity in a Methandiide-Derived Iridium Carbene Complex." Chemistry - A European Journal 22, no. 11 (January 8, 2016): 3846–55. http://dx.doi.org/10.1002/chem.201503936.

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8

Iwasaki, Fujiko, Masanori Yasui, Satoshi Yoshida, Hideyuki Nishiyama, Souichi Shimamoto, and Noboru Matsumura. "Crystal and Molecular Structures of Novel Metal–Carbene Complexes III. Rh–Carbene Complexes and Cu Complex." Bulletin of the Chemical Society of Japan 69, no. 10 (October 1996): 2759–70. http://dx.doi.org/10.1246/bcsj.69.2759.

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9

Zhang, Le, and Ying-Feng Han. "A macrocyclic silver polycarbene complex based on 1,2,4-triazole units: synthesis and postsynthetic modification." Dalton Transactions 47, no. 12 (2018): 4267–72. http://dx.doi.org/10.1039/c8dt00169c.

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10

SINHA, ARUP, ABIR SARBAJNA, SHRABANI DINDA, and JITENDRA K. BERA. "A RhIII–N-heterocyclic carbene complex from metal–metal singly bonded [RhII −RhII] precursor." Journal of Chemical Sciences 123, no. 6 (November 2011): 799–805. http://dx.doi.org/10.1007/s12039-011-0161-9.

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11

Bidal, Yannick D., Mathieu Lesieur, Mohand Melaimi, David B. Cordes, Alexandra M. Z. Slawin, Guy Bertrand, and Catherine S. J. Cazin. "A simple access to transition metal cyclopropenylidene complexes." Chemical Communications 51, no. 23 (2015): 4778–81. http://dx.doi.org/10.1039/c4cc10375k.

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The first example of a BAC–Cu complex, its outstanding catalytic activity in Click chemistry and its use as a carbene-transfer reagent to easily access Au-, Pd–, Ir– and Rh–BAC compounds are reported.

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12

González-Herrero, Pablo, Birgit Weberndörfer, Kerstin Ilg, Justin Wolf, and Helmut Werner. "The First Example of an Equilibrium between a Carbene and an Isomeric Carbyne Transition Metal Complex." Angewandte Chemie 39, no. 18 (September 15, 2000): 3266–69. http://dx.doi.org/10.1002/1521-3773(20000915)39:18<3266::aid-anie3266>3.0.co;2-#.

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13

Li, Yanjun, Meng Lei, Wei Yuan, Eric Meggers, and Lei Gong. "An N-heterocyclic carbene iridium catalyst with metal-centered chirality for enantioselective transfer hydrogenation of imines." Chemical Communications 53, no. 57 (2017): 8089–92. http://dx.doi.org/10.1039/c7cc04691j.

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14

Le Bozec, Hubert, Jean-Luc Fillaut, and Pierre H. Dixneuf. "Metal to carbene 1,2 hydrogen migration in the protonation of a fischer-type carbene iron(0) complex." Journal of the Chemical Society, Chemical Communications, no. 15 (1986): 1182. http://dx.doi.org/10.1039/c39860001182.

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15

Carson, Fabian, Elisa Martínez-Castro, Rocío Marcos, Greco González Miera, Kjell Jansson, Xiaodong Zou, and Belén Martín-Matute. "Effect of the functionalisation route on a Zr-MOF with an Ir–NHC complex for catalysis." Chemical Communications 51, no. 54 (2015): 10864–67. http://dx.doi.org/10.1039/c5cc03934g.

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A new iridium N-heterocyclic carbene (NHC) metallolinker has been synthesised and introduced into a metal–organic framework (MOF), for the first time, via two different routes: direct synthesis and postsynthetic exchange (PSE).

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16

Bhunia, Mrinal, Sumeet Ranjan Sahoo, Arpan Das, Jasimuddin Ahmed, Sreejyothi P., and Swadhin K. Mandal. "Transition metal-free catalytic reduction of primary amides using an abnormal NHC based potassium complex: integrating nucleophilicity with Lewis acidic activation." Chemical Science 11, no. 7 (2020): 1848–54. http://dx.doi.org/10.1039/c9sc05953a.

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An abnormal N-heterocyclic carbene (aNHC) based potassium complex was used as a transition metal-free catalyst for reduction of primary amides to corresponding primary amines under ambient conditions.

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17

Zhang, Jing-Jing, Julienne K. Muenzner, Mohamed A. Abu el Maaty, Bianka Karge, Rainer Schobert, Stefan Wölfl, and Ingo Ott. "A multi-target caffeine derived rhodium(i) N-heterocyclic carbene complex: evaluation of the mechanism of action." Dalton Transactions 45, no. 33 (2016): 13161–68. http://dx.doi.org/10.1039/c6dt02025a.

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A rhodium(i) and a ruthenium(ii) complex with a caffeine derived N-heterocyclic carbene (NHC) ligand were biologically investigated as organometallic conjugates consisting of a metal center and a naturally occurring moiety.

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18

Laus, Gerhard, Klaus Wurst, Volker Kahlenberg, Holger Kopacka, Christoph Kreutz, and Herwig Schottenberger. "N-Heterocyclic Carbene (NHC) Derivatives of 1,3-Di(benzyloxy)imidazolium Salts." Zeitschrift für Naturforschung B 65, no. 7 (July 1, 2010): 776–82. http://dx.doi.org/10.1515/znb-2010-0702.

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1-Hydroxyimidazole-3-oxide (1) was alkylated with benzyl bromide in the presence of NaHCO3 to give the new 1,3-di(benzyloxy)imidazolium bromide 2a which was converted to the hexafluorophosphate 2b and bis(trifluoromethylsulfonyl)imide 2c. From this cation, pyridine generated a carbene which was trapped by sulfur or selenium to yield the respective 2-thione 3 or 2-selone 4. Bromination afforded the 2-bromo derivative 5. Reaction of the hexafluorophosphate 2b with silver oxide gave the silver-N-heterocyclic carbene complex 6 which was transmetallated with Au(Me2S)Cl to the gold-carbene complex 7. A rhodium-carbene complex 8 was obtained by reaction of the hexafluorophosphate 2b with [Rh(cod)Cl]2 in the presence of triethylamine. Eight crystal structures were determined by X-ray diffraction. The N-benzyloxy groups are twisted out of the plane of the imidazole ring in the solid state. They adopt syn conformations in the cation of the hexafluorophosphate 2b and in the metal-carbene complexes 6 - 8, but anti conformations in the thione 3 and selone 4. Both conformations were observed in two polymorphs of the 2-bromo compound 5.

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19

Gründemann, Stephan, Anes Kovacevic, Martin Albrecht, Jack W. Faller Robert, and H. Crabtree. "Abnormal binding in a carbene complex formed from an imidazolium salt and a metal hydride complex." Chemical Communications, no. 21 (2001): 2274. http://dx.doi.org/10.1039/b107881j.

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20

Mazzoni, Rita, Fabio Marchetti, Andrea Cingolani, and Valerio Zanotti. "Bond Forming Reactions Involving Isocyanides at Diiron Complexes." Inorganics 7, no. 3 (February 26, 2019): 25. http://dx.doi.org/10.3390/inorganics7030025.

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The versatility of isocyanides (CNR) in organic chemistry has been tremendously enhanced by continuous advancement in transition metal catalysis. On the other hand, the urgent need for new and more sustainable synthetic strategies based on abundant and environmental-friendly metals are shifting the focus towards iron-assisted or iron-catalyzed reactions. Diiron complexes, taking advantage of peculiar activation modes and reaction profiles associated with multisite coordination, have the potential to compensate the lower activity of Fe compared to other transition metals, in order to activate CNR ligands. A number of reactions reported in the literature shows that diiron organometallic complexes can effectively assist and promote most of the “classic” isocyanide transformations, including CNR conversion into carbyne and carbene ligands, CNR insertion, and coupling reactions with other active molecular fragments in a cascade sequence. The aim is to evidence the potential offered by diiron coordination of isocyanides for the development of new and more sustainable synthetic strategies for the construction of complex molecular architectures.

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21

Jahnke, Mareike C., and Ekkehardt Hahn. "Platinum Complexes with Picoline-functionalized Benzimidazolin-2-ylidene Ligands." Zeitschrift für Naturforschung B 65, no. 3 (March 1, 2010): 341–46. http://dx.doi.org/10.1515/znb-2010-0318.

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The dicarbene platinum complexes of the type [Pt(L)2]Br2 [5]Br2 - [8]Br2 (L = N-alkyl-N´- picolylbenzimidazolin-2-ylidene) have been prepared by two different methods. The in situ deprotonation of picoline-functionalized benzimidazolium salts 1 - 4 with platinum acetylacetonate gave the platinum complexes [5]Br2 - [8]Br2 in good yields. Complex [8]Br2 has also been obtained by a ligand transfer reaction from the silver dicarbene complex [9][AgBr2]. Attempts to cystallize [8]Br2 obtained from the carbene transfer reaction led to the isolation of the previously undetected monocarbene complex [Pt(Cl)2L] (10) which contains only one picoline-functionalized carbene ligand coordinating in a chelating fashion to the metal center

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22

Demonceau, Albert, Alfred F. Noels, Jean-Louis Costa, and André J. Hubert. "Rhodium(II) carboxylate-catalysed reactions of diazoesters: evidence for an equilibrium between free carbene and a metal-carbene complex." Journal of Molecular Catalysis 58, no. 1 (January 1990): 21–26. http://dx.doi.org/10.1016/0304-5102(90)85176-i.

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23

Coleman, Karl S., Sarim Dastgir, Guy Barnett, Maria J. P. Alvite, Andrew R. Cowley, and Malcolm L. H. Green. "A nonenolizable imino-N-heterocyclic carbene ligand and corresponding silver (I) metal complex." Journal of Organometallic Chemistry 690, no. 24-25 (December 2005): 5591–96. http://dx.doi.org/10.1016/j.jorganchem.2005.07.020.

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24

Inoue, Shigeyoshi, and Carsten Eisenhut. "A Dihydrodisilene Transition Metal Complex from an N-Heterocyclic Carbene-Stabilized Silylene Monohydride." Journal of the American Chemical Society 135, no. 49 (November 22, 2013): 18315–18. http://dx.doi.org/10.1021/ja410528y.

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25

Daran, Jean-Claude, Funda Demirhan, Özgür Yıldırım, and Bekir Çetinkaya. "1-Ferrocenylmethyl-3-(2,4,6-trimethylbenzyl)-1H-imidazolidin-3-ium iodide andtrans-bis(3-benzyl-1-ferrocenylmethyl-1H-imidazolidin-2-ylidene)diiodidopalladium(II)." Acta Crystallographica Section C Crystal Structure Communications 68, no. 2 (January 25, 2012): m48—m52. http://dx.doi.org/10.1107/s0108270112000601.

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Owing to increasing interest in the use of N-heterocyclic carbenes (NHCs) based on imidazolidinium ions as ligands in the design of highly efficient transition-metal-based homogeneous catalysts, the characterizations of the 1-ferrocenylmethyl-3-(2,4,6-trimethylbenzyl)imidazolidin-3-ium iodide salt, [Fe(C5H5)(C19H24N2)]I, (I), and the palladium complextrans-bis(3-benzyl-1-ferrocenylmethyl-1H-imidazolidin-2-ylidene)diiodidopalladium(II), [Fe2Pd(C5H5)2(C16H17N2)2I2], (II), are reported. Compound (I) has two iodide anions and two imidazolidinium cations within the asymmetric unit (Z′ = 2). The two cations have distinctly different conformations, with the ferrocene groups orientatedexoandendowith respect to the N-heterocyclic carbene. Weak C—H donor hydrogen bonds to both the iodide anions and the π system of the mesitylene group combine to form two-dimensional layers perpendicular to the crystallographiccdirection. Only one of the formally charged imidazolidinium rings forms a near-linear hydrogen bond with an iodide anion. Complex (II) shows square-planar coordination around the PdIImetal, which is located on an inversion centre (Z′ = 0.5). The ferrocene and benzyl substituents are in atrans–antiarrangement. The Pd—C bond distance between the N-heterocyclic carbene ligands and the metal atom is 2.036 (7) Å. A survey of related structures shows that the lengthening of the N—C bonds and the closure of the N—C—N angle seen here on metal complexation is typical of similar NHCs and their complexes.

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26

Weismann, Julia, and Viktoria H. Gessner. "Si–H activation by means of metal ligand cooperation in a methandiide derived carbene complex." Chemical Communications 51, no. 80 (2015): 14909–12. http://dx.doi.org/10.1039/c5cc05201g.

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27

Liu, Shao Bo, Cheng Yi, Hong Ying Xia, and Feng Zhao. "Synthesis and Photophysical Properties of New Three-Coordinate N-Heterocyclic Carbene Copper Complex." Materials Science Forum 878 (November 2016): 18–21. http://dx.doi.org/10.4028/www.scientific.net/msf.878.18.

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A three-coordinateopper (I) complex supported by N-heterocyclic carbene (NHC) ligand and bis [2-(diphenylphosphino) phenyl] ether (POP) ligand were successfully reported and characterized. The corresponding photophysical properties were investigated using UV-vis and emission spectrometry. The lowest-energy absorption band at 343 nm was assigned to metal-to-ligand charge transfer (MLCT) transtion. The emission maximum located at 470 nm upon excitation at 290 nm in PMMA films at room temperature originates from the typical 3MLCT excited state.

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28

Hagen, Dirk J., Ian M. Povey, Simon Rushworth, Jacqueline S. Wrench, Lynette Keeney, Michael Schmidt, Nikolay Petkov, Seán T. Barry, Jason P. Coyle, and Martyn E. Pemble. "Atomic layer deposition of Cu with a carbene-stabilized Cu(i) silylamide." J. Mater. Chem. C 2, no. 43 (2014): 9205–14. http://dx.doi.org/10.1039/c4tc01418a.

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The metal–organic Cu(i) complex 1,3-diisopropyl-imidazolin-2-ylidene copper hexamethyl disilazide has been tested as a novel oxygen-free precursor for atomic layer deposition of Cu with molecular hydrogen.

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29

Weber, Lothar, Iris Schumann, Matthias H. Scheffer, Hans-Georg Stammler, and Beate Neumann. "Übergangsmetall-substituierte Acylphosphane und Phosphaalkene, XXXIY [1] Methylendiyl(thioxo)- und MethyIendiyl(selenoxo)-λ5,σ3-phosphorane als μ-Liganden in [(η5-C5H5)2Fe2(CO)3]-Komplexen. Synthese und Struktur von / Transition Metal Substituted Acylphosphanes and Phosphaalkenes, XXXIV [1] Methylenediyl(thioxo)- and M ethylenediyl(selenoxo)-λ5 ,σ3-phosphoranes as μ-Ligands in [(η5-C5H5)2Fe2(CO)3] Complexes. Synthesis and Structure of." Zeitschrift für Naturforschung B 52, no. 5 (May 1, 1997): 655–62. http://dx.doi.org/10.1515/znb-1997-0519.

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Abstract The isophosphaalkyne complex (η5-C5H5)2(CO)2Fe2 (μ-CO)(μ-C=PMes) (2a) was converted into the methylenediyl(thioxo)- and methylenediyl(selenoxo)- λ5, σ3-phosphorane complexes (η5-C5H5)2(CO)2Fe2(μ-CO)(μ-C=P(E)Mes) (5a: E = S; 5b E = Se) by oxidation with sulfur or selenium . Reaction of the μ-carbyne complex [(μ75-C5H5)2(CO)2Fe2(μ-CO)(μ- CSMe)]+SO3CF3 (1) with tBuP(H)SiMe3 in the presence of DBU afforded the μ-phosphinocarbyne complex (η5-C5H5)2(CO)2Fe2(μ-CP(H)tBu] (μ -SMe] (12). μ-Carbene complex (11) was isolated as an initial product of this conversion and fully characterized by single crystal X-ray analysis.

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30

Yuan, Jian, Russell P. Hughes, and Arnold L. Rheingold. "The First Example of a Bis(trifluoromethyl)carbene Transition-Metal Complex and Its Reduction to a Perfluoroallene Complex." European Journal of Inorganic Chemistry 2007, no. 30 (October 2007): 4723–25. http://dx.doi.org/10.1002/ejic.200700814.

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31

Fehlhammer, Wolf P., and Gerhard Beck. "Metallkomplexe funktioneller Isocyanide, XVIII [1]. (Alkylidenamino)carbene durch nucleophile Addition an Pentacarbonylchrom-koordiniertes 1,1-Dichlormethyl-, 1,1,2-Trichlorethyl- und 1-Chlorvinylisocyanid / Metal Complexes of Functional Isocyanides, XVIII [1]. (Alkylideneamino)carbenes by Nucleophilic Addition to Pentacarbonylchromium-coordinated 1,1-Dichloromethyl, 1,1,2-Trichloroethyl and 1-Chlorovinyl Isocyanide." Zeitschrift für Naturforschung B 44, no. 11 (November 1, 1989): 1414–20. http://dx.doi.org/10.1515/znb-1989-1116.

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Pyrrolidine adds to the isocyano group of Cr(CO)5CNCCl2CH2Cl with concomitant loss of HC1 to give a (1,2-dichloroethylideneamino)(pyrrolidino)carbene complex in which the α-chlorine atom can be replaced by a second molecule of pyrrolidine. Cr(CO)5CNCCl2H (2) and Cr(CO)5CNCCl= CH2 (4) only afford the respective 1:2 adducts, 4 also with diethylamine. 2 and t-butanethiol react with formation of a (t-butylthiomethylidenamino)(t-butylthio)carbene complex (main product) and Cr(CO)5CNCH2Cl (side product). The IR spectra of the carbene species show unusual v(CO) patterns. In order to explain the NMR spectra, three different kinds of hindered rotations and a fast nitrogen inversion are proposed.

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32

Streubel, Rainer, Markus Hobbold, and Siegfried Priemer. "Synthesis of the first stable Fischer-type carbene metal complex with a COP structural motive of the carbene ligand." Journal of Organometallic Chemistry 613, no. 1 (October 2000): 56–59. http://dx.doi.org/10.1016/s0022-328x(00)00454-x.

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33

Ghadwal, Rajendra S., Dennis Rottschäfer, Diego M. Andrada, Gernot Frenking, Christian J. Schürmann, and Hans-Georg Stammler. "Normal-to-abnormal rearrangement of an N-heterocyclic carbene with a silylene transition metal complex." Dalton Transactions 46, no. 24 (2017): 7791–99. http://dx.doi.org/10.1039/c7dt01199g.

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The NHC ligand of the complex 3-W undergoes normal-to-abnormal rearrangement on treatment with CsOH and yields the aNHC-complex 6-W, which is found to be 13.5 kcal mol⁻¹ less stable than its normal counterpart.

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34

Li, Mao-Lin, Jin-Han Yu, Yi-Hao Li, Shou-Fei Zhu, and Qi-Lin Zhou. "Highly enantioselective carbene insertion into N–H bonds of aliphatic amines." Science 366, no. 6468 (November 21, 2019): 990–94. http://dx.doi.org/10.1126/science.aaw9939.

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Aliphatic amines strongly coordinate, and therefore easily inhibit, the activity of transition-metal catalysts, posing a marked challenge to nitrogen-hydrogen (N–H) insertion reactions. Here, we report highly enantioselective carbene insertion into N–H bonds of aliphatic amines using two catalysts in tandem: an achiral copper complex and chiral amino-thiourea. Coordination by a homoscorpionate ligand protects the copper center that activates the carbene precursor. The chiral amino-thiourea catalyst then promotes enantioselective proton transfer to generate the stereocenter of the insertion product. This reaction couples a wide variety of diazo esters and amines to produce chiral α-alkyl α–amino acid derivatives.

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35

Altmann, Philipp J., Michael Ehrenreich, and Alexander Pöthig. "A hybrid imidazolylidene/imidazolium nickel NHC complex: an isolated intermediate." Acta Crystallographica Section C Structural Chemistry 73, no. 11 (October 6, 2017): 880–84. http://dx.doi.org/10.1107/s2053229617013250.

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Macrocyclic ligand systems with a variety of (different) donor sites oftentimes give rise to very exciting and unexpected multinuclear metal complexes. We report herein the structure of a trinuclear mixed imidazolylidene/imidazolium nickel N-heterocyclic carbene (NHC) complex, namely di-μ-chlorido-bis{μ-calix[2]imidazolium[2]imidazolylidene[2]pyrazolate}trinickel(II) tetrakis(hexafluoridophosphate) acetonitrile tetrasolvate, [Ni3(C24H24N12)2Cl2](PF6)4·4CH3CN or [Ni3(L Me)2Cl2](PF6)4·4CH3CN, that can be understood as a trapped reaction intermediate during the synthesis of the respective [Ni2 L Me](PF6)2 product. The structure not only contains protonated next to deprotonated imidazole heterocycles, but also Ni2+ ions with fundamentally different coordination modes within one molecule. Two of the three metal atoms are coordinated in a square-pyramidal fashion by half a ligand molecule and one chloride ligand, whereas the third Ni2+ ion is bound octahedrally by four pyrazolate moieties and two chloride anions.

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36

Harlepp, Sébastien, Edith Chardon, Mathilde Bouché, Georges Dahm, Mounir Maaloum, and Stéphane Bellemin-Laponnaz. "N-Heterocyclic Carbene-Platinum Complexes Featuring an Anthracenyl Moiety: Anti-Cancer Activity and DNA Interaction." International Journal of Molecular Sciences 20, no. 17 (August 27, 2019): 4198. http://dx.doi.org/10.3390/ijms20174198.

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A platinum (II) complex stabilized by a pyridine and an N-heterocyclic carbene ligand featuring an anthracenyl moiety was prepared. The compound was fully characterized and its molecular structure was determined by single-crystal X-ray diffraction. The compound demonstrated high in vitro antiproliferative activities against cancer cell lines with IC50 ranging from 10 to 80 nM. The presence of the anthracenyl moiety on the N-heterocyclic carbene (NHC) Pt complex was used as a luminescent tag to probe the metal interaction with the nucleobases of the DNA through a pyridine-nucleobase ligand exchange. Such interaction of the platinum complex with DNA was corroborated by optical tweezers techniques and liquid phase atomic force microscopy (AFM). The results revealed a two-state interaction between the platinum complex and the DNA strands. This two-state behavior was quantified from the different experiments due to contour length variations. At 24 h incubation, the stretching curves revealed multiple structural breakages, and AFM imaging revealed a highly compact and dense structure of platinum complexes bridging the DNA strands.

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37

Kjær, Kasper Skov, Nidhi Kaul, Om Prakash, Pavel Chábera, Nils W. Rosemann, Alireza Honarfar, Olga Gordivska, et al. "Luminescence and reactivity of a charge-transfer excited iron complex with nanosecond lifetime." Science 363, no. 6424 (November 29, 2018): 249–53. http://dx.doi.org/10.1126/science.aau7160.

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Iron’s abundance and rich coordination chemistry are potentially appealing features for photochemical applications. However, the photoexcitable charge-transfer states of most iron complexes are limited by picosecond or subpicosecond deactivation through low-lying metal-centered states, resulting in inefficient electron-transfer reactivity and complete lack of photoluminescence. In this study, we show that octahedral coordination of iron(III) by two mono-anionic facialtris-carbene ligands can markedly suppress such deactivation. The resulting complex [Fe(phtmeimb)2]+, where phtmeimb is {phenyl[tris(3-methylimidazol-1-ylidene)]borate}−, exhibits strong, visible, room temperature photoluminescence with a 2.0-nanosecond lifetime and 2% quantum yield via spin-allowed transition from a doublet ligand-to-metal charge-transfer (2LMCT) state to the doublet ground state. Reductive and oxidative electron-transfer reactions were observed for the2LMCT state of [Fe(phtmeimb)2]+in bimolecular quenching studies with methylviologen and diphenylamine.

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38

Heinz Dötz, Karl, Philipp Tomuschat, and Martin Nieger. "Reactions of Complex Ligands, LXXVII. Axial-Chiral Metal Carbenes: Synthesis and Structure of 1,1-Binaphthyl-Derived Carbonyl-Carbene Complexes of Chromium." Chemische Berichte 130, no. 11 (November 1997): 1605–9. http://dx.doi.org/10.1002/cber.19971301108.

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39

Byrne, Joseph P., Pauline Musembi, and Martin Albrecht. "Carbohydrate-functionalized N-heterocyclic carbene Ru(ii) complexes: synthesis, characterization and catalytic transfer hydrogenation activity." Dalton Transactions 48, no. 31 (2019): 11838–47. http://dx.doi.org/10.1039/c9dt02614b.

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Triazolylidene NHCs decorated with a carbohydrate wingtip group were complexed to a ruthenium(ii) center. Deprotection of the carbohydrate in the metal complex affords a carbohydrate–NHC hybrid system for use as a transfer hydrogenation catalyst.

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40

Al Thagfi, Jameel, and Gino G. Lavoie. "Density functional theory study of bis(imino) N-heterocyclic carbene iron(II) complexes." Canadian Journal of Chemistry 92, no. 10 (October 2014): 925–31. http://dx.doi.org/10.1139/cjc-2014-0022.

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Density functional theory calculations at the B3LYP/DGDZVP and UB3LYP/TZVP levels were performed on 1,3-bis[1-(2,6-dimethylphenylimino)ethyl]imidazolium and on the corresponding imidazol-2-ylidene iron(II) dichloride complex, respectively. The resulting geometrical parameters of the optimized structures were in good agreement with previously reported X-ray structures. The ground state for the high-spin (quintet multiplicity) iron complex is 82.4 kJ/mol lower in energy compared to the low-spin (triplet) configuration, in agreement with magnetic susceptibility measurements. Further calculations were carried out on related benzimidazol-2-ylidene and pyrimidin-2-ylidene ligands and on the corresponding iron complexes to gain insight into their electronic properties and reactivities. The energy of the highest occupied and lowest unoccupied molecular orbitals of all three carbenes suggests that the pyrimidin-2-ylidene and the benzimidazol-2-ylidene are the best σ-donor and best π-acceptor, respectively. Using those results, the metal center in the pyrimidin-2-ylidene iron dichloride complex was predicted to bear the highest electron density. This was supported by the high relative energy of its highest occupied molecular orbital compared to that of the corresponding imidazole-2-ylidene and benzimidazol-2-ylidene iron complexes. The electrostatic potential maps of all three metal complexes furthermore indicated a marked decrease in electron density for the coordinated imine group, supporting a greater reactivity towards nucleophiles.

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41

Riener, Korbinian, Alexander Pöthig, Mirza Cokoja, Wolfgang A. Herrmann, and Fritz E. Kühn. "Structure and spectroscopic properties of the dimeric copper(I) N-heterocyclic carbene complex [Cu2(CNCt-Bu)2](PF6)2." Acta Crystallographica Section C Structural Chemistry 71, no. 8 (July 7, 2015): 643–46. http://dx.doi.org/10.1107/s2053229615012140.

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In recent years, the use of copper N-heterocyclic carbene (NHC) complexes has expanded to fields besides catalysis, namely medicinal chemistry and luminescence applications. In the latter case, multinuclear copper NHC compounds have attracted interest, however, the number of these complexes in the literature is still quite limited. Bis[μ-1,3-bis(3-tert-butylimidazolin-2-yliden-1-yl)pyridine]-1κ4C2,N:N,C2′;2κ4C2,N:N,C2′-dicopper(I) bis(hexafluoridophosphate), [Cu2(C19H25N5)2](PF6)2, is a dimeric copper(I) complex bridged by two CNC,i.e.bis(N-heterocyclic carbene)pyridine, ligands. Each CuIatom is almost linearly coordinated by two NHC ligands and interactions are observed between the pyridine N atoms and the metal centres, while no cuprophilic interactions were observed. Very strong absorption bands are evident in the UV–Vis spectrum at 236 and 274 nm, and an emission band is observed at 450 nm. The reported complex is a new example of a multinuclear copper NHC complex and a member of a compound class which has only rarely been reported.

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42

Sinha, Arup, Prosenjit Daw, S. M. Wahidur Rahaman, Biswajit Saha, and Jitendra K. Bera. "A RuII–N-heterocyclic carbene (NHC) complex from metal–metal singly bonded diruthenium(I) precursor: Synthesis, structure and catalytic evaluation." Journal of Organometallic Chemistry 696, no. 6 (March 2011): 1248–57. http://dx.doi.org/10.1016/j.jorganchem.2010.11.003.

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43

Duan, Wenzeng, Yudao Ma, Yanmin Huo, and Qingxia Yao. "Crystal Structure Studies towards the Synthesis and Applications of N-heterocyclic Carbene–Metal Complexes Derived from [2.2]Paracyclophane." Australian Journal of Chemistry 68, no. 10 (2015): 1472. http://dx.doi.org/10.1071/ch15002.

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The crystal structures of six planar chiral N-heterocyclic carbene (NHC) precursors and one NHC–Rh complex derived from [2.2]paracyclophane were described. The NHC–metal complexes were prepared to examine their catalytic activities toward the Rh-catalyzed asymmetric addition of phenylboronic acid to 1-naphthaldehyde. The results were correlated to the single-crystal crystallographic studies. The novel NHC precursor 5 can achieve high catalytic activity in the asymmetric addition of phenylboronic acid to 1-naphthaldehyde.

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44

Faller, Jack W., and Philip P. Fontaine. "Synthesis and characterization of a planar chiral and chiral-at-metal ruthenium N-heterocyclic carbene complex." Journal of Organometallic Chemistry 691, no. 26 (December 2006): 5798–803. http://dx.doi.org/10.1016/j.jorganchem.2006.09.041.

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45

DOETZ, K. H., R. EHLENZ, and D. PAETSCH. "ChemInform Abstract: Organo-Transition-Metal Modified Sugars. Part 7. Carbene Complex Modified Glycals: Synthesis and Reactivity." ChemInform 29, no. 7 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199807236.

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46

Hsieh, Chung-Hung, Randara Pulukkody, and Marcetta Y. Darensbourg. "A dinitrosyl iron complex as a platform for metal-bound imidazole to N-heterocyclic carbene conversion." Chemical Communications 49, no. 81 (2013): 9326. http://dx.doi.org/10.1039/c3cc45091k.

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47

Daubit, Isabelle Marie, and Nils Metzler-Nolte. "On the interaction of N-heterocyclic carbene Ir+I complexes with His and Cys containing peptides." Dalton Transactions 48, no. 36 (2019): 13662–73. http://dx.doi.org/10.1039/c9dt01338e.

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In the interaction of an [Ir(+i)(COD)(NHC)Cl] complex with model peptides a chelating motif with a particularly interesting bimetallic peptide-bridged Ir(+iii)–NHC motif was identified with loss of the COD and Cl ligands and oxidation of the metal.

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48

Chen, Jia-Bi, Gui-Xin Lei, Ze-Ying Zhang, and You-Qi Tang. "Transition metal carbene complexes: IV. Synthesis and crystal structure of a novel iron-sulfur cluster carbene complex of rhenium-π-cyclopentadienyl(dicarbonyl)-{phenyl[(μ-phenylthio)hexacarbonyldiiron-(μ-thio)]carbene}rhenium." Acta Chimica Sinica 4, no. 4 (December 1986): 311–19. http://dx.doi.org/10.1002/cjoc.19860040405.

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49

Walley, Jacob E., Yuen-Onn Wong, Lucas A. Freeman, Diane A. Dickie, and Robert J. Gilliard. "N-Heterocyclic Carbene-Supported Aryl- and Alk- oxides of Beryllium and Magnesium." Catalysts 9, no. 11 (November 8, 2019): 934. http://dx.doi.org/10.3390/catal9110934.

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Recently, we have witnessed significant progress with regard to the synthesis of molecular alkaline earth metal reagents and catalysts. To provide new precursors for light alkaline earth metal chemistry, molecular aryloxide and alkoxide complexes of beryllium and magnesium are reported. The reaction of beryllium chloride dietherate with two equivalents of 1,3-diisopropyl-4,5-dimethylimidizol-2-ylidine (sIPr) results in the formation of a bis(N-heterocyclic carbene) (NHC) beryllium dichloride complex, (sIPr)2BeCl2 (1). Compound 1 reacts with lithium diisopropylphenoxide (LiODipp) or sodium ethoxide (NaOEt) to form the terminal aryloxide (sIPr)Be(ODipp)2 (2) and alkoxide dimer [(sIPr)Be(OEt)Cl]2 (3), respectively. Compounds 2 and 3 represent the first beryllium alkoxide and aryloxide species supported by NHCs. Structurally related dimers of magnesium, [(sIPr)Mg(OEt)Brl]2 (4) and [(sIPr)Mg(OEt)Me]2 (5), were also prepared. Compounds 1-5 were characterized by single crystal X-ray diffraction studies, 1H, 13C, and 9Be NMR spectroscopy where applicable.

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50

Bertini, Simone, and Martin Albrecht. "O-Functionalised NHC Ligands for Efficient Nickel-catalysed C–O Hydrosilylation." CHIMIA International Journal for Chemistry 74, no. 6 (June 24, 2020): 483–88. http://dx.doi.org/10.2533/chimia.2020.483.

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A series of C,O-bidentate chelating mesoionic carbene nickel(ii) complexes [Ni(NHC^PhO)2] (NHC = imidazolylidene or triazolylidene) were applied for hydrosilylation of carbonyl groups. The catalytic system is selective towards aldehyde reduction and tolerant to electron-donating and -withdrawing group substituents. Stoichiometric experiments in the presence of different silanes lends support to a metal–ligand cooperative activation of the Si–H bond. Catalytic performance of the nickel complexes is dependent on the triazolylidene substituents. Butyl-substituted triazolylidene ligands impart turnover numbers up to 7,400 and turnover frequencies of almost 30,000 h-1, identifying this complex as one of the best-performing nickel catalysts for hydrosilylation and demonstrating the outstanding potential of O-functionalised NHC ligands in combination with first-row transition metals.

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