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Journal articles on the topic 'Carbene precursor'

Author: Grafiati

Published: 4 June 2021

Last updated: 8 February 2022

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1

Chowdhury, Rajdip, and Abraham Mendoza. "N-Hydroxyphthalimidyl diazoacetate (NHPI-DA): a modular methylene linchpin for the C–H alkylation of indoles." Chemical Communications 57, no. 37 (2021): 4532–35. http://dx.doi.org/10.1039/d1cc01026c.

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The insertion of conventional diazocompounds into indoles are still limited by the custom carbene precursors, catalysts and manipulation of the products required. Herein, we address these shortcomings with a redox-active carbene precursor (NHPI-DA).

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2

Blanch, Rodney J., and Curt Wentrup. "Trifluoromethylphenylcarbenes. Carbene-Carbene Interconversion on the Singlet Energy Surface and Rearrangement to Trifluorobenzocyclobutene, Trifluorostyrene, and Trifluoromethylfulvenallenes." Australian Journal of Chemistry 68, no. 1 (2015): 36. http://dx.doi.org/10.1071/ch14097.

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The four isomeric α-, ortho-, meta-, and para-trifluoromethylphenylcarbenes were generated by photolysis of the corresponding 3-phenyl-3-trifluoromethyldiazirene 1 or the four isomeric trifluoromethylphenyldiazomethanes 2 and 4–6. The four corresponding triplet trifluoromethylphenylcarbenes 3 and 7–9 were observed by electron spin resonance (ESR) spectroscopy in Ar matrices at 14 K. The α- and ortho-carbenes 3 and 7 and the ortho- and para-carbenes 7 and 9 interconvert partially when generated by short-wavelength photolysis (350 nm) before intersystem crossing to the triplet states. The triplet states do not undergo further Carbene-Carbene interconversion. The interconversions are assumed to take place via the meta-trifluoromethylphenylcarbene 8. When the ortho- and para-carbenes are generated by long-wavelength photolysis (>450 nm), the discrete, non-interconverting triplet carbenes are observed in the ESR spectra. Flash vacuum thermolysis of the diazirene 1 at 500°C afforded a mixture of bis(trifluoromethyl)heptafulvalenes 11, bis(trifluoromethyl)stilbenes 12, and bis(trifluoromethyl)anthracenes 13, and the presence of their likely precursor(s), trifluoromethylcycloheptatetraene(s), was confirmed by a peak at 1830 cm–1 in the Ar matrix IR spectrum. In addition, at 700°C, four monomeric carbene rearrangement products were isolated and characterised, viz. 1,1,2-trifluorobenzocyclobutene 14, 1′,2′,2′-trifluorostyrene 15, and 1- and 2-trifluoromethylfulvenallenes 16 and 17.

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3

Hudnall, Todd W., Eric W. Reinheimer, and Christopher L. Dorsey. "Synthesis, crystal structure determination, and spectroscopic analyses of 1-chloro-2-(2,6-diisopropylphenyl)-4,4-dimethyl-2-azaspiro[5.5]undecane-3,5-dione: an unyielding precursor to a cyclic (alkyl)(amido)carbene." Acta Crystallographica Section C Structural Chemistry 77, no. 7 (June 25, 2021): 411–19. http://dx.doi.org/10.1107/s2053229621006173.

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The synthesis, single-crystal X-ray structure, and 1H and 13C NMR spectrocopic analyses of an unyielding precursor molecule to a cyclic (alkyl)(amido)carbene, 1-chloro-2-(2,6-diisopropylphenyl)-4,4-dimethyl-2-azaspiro[5.5]undecane-3,5-dione, C24H34ClNO2 (1), is reported. Despite the use of several bases, 1 could not be deprotonated to afford the corresponding carbene. The crystal structure of 1 was compared to the crystal structures of two structurally similar HCl adducts of stable carbenes (compounds 4 and 5), which revealed no significant differences in the geometries about the `carbene' C atoms. To better understand the reactivity differences observed for 1 when compared to 4 and 5, modified percent buried volume (%V bur) calculations were performed. These calculations revealed that the H atom bound to the carbene C atom is the most sterically hindered in compound 1 when compared to 4 and 5 (%V bur = 84.9, 81.3, and 79.3% for 1, 4, and 5, respectively). Finally, close inspection of the quadrant-specific %V bur values indicated that the approach of a deprotonating base to the H atom bound to the carbene C atom is significantly blocked in 1 (69.9%) when compared to 4 and 5 (50.4 and 56.5%, respectively).

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4

Ren, Li, Austin C. Chen, Andreas Decken, and Cathleen M. Crudden. "Chiral bidentate N-heterocyclic carbene complexes of Rh and Pd." Canadian Journal of Chemistry 82, no. 12 (December 1, 2004): 1781–87. http://dx.doi.org/10.1139/v04-165.

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The synthesis of a new chiral, bidentate oxazoline/imidazolidene carbene precursor is described. This species is reacted with various metal salts in the presence of a base to generate rhodium and palladium complexes, which are characterized spectroscopically and crystallographically.Key words: chiral N-heterocyclic carbene, rhodium, palladium, oxazolidine, asymmetric catalysis.

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5

Holm, Stefanie C., Frank Rominger, and Bernd F. Straub. "Thiol-functionalized 1,2,4-triazolium salt as carbene ligand precursor." Journal of Organometallic Chemistry 719 (November 2012): 54–63. http://dx.doi.org/10.1016/j.jorganchem.2012.08.018.

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6

Jenks, William S., Melanie J. Heying, and Erin M. Rockafellow. "Modulation of Carbene Spin State Population through Precursor Photophysics." Organic Letters 11, no. 4 (February 19, 2009): 955–58. http://dx.doi.org/10.1021/ol802934w.

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7

Gilliom, Laura R., and Robert H. Grubbs. "A titanacyclobutane precursor to alkyl-substituted titanium carbene complexes." Organometallics 5, no. 4 (April 1986): 721–24. http://dx.doi.org/10.1021/om00135a016.

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8

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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9

Tang, Z., S. Mandal, N. D. Paul, M. Lutz, P. Li, J. I. van der Vlugt, and B. de Bruin. "Rhodium catalysed conversion of carbenes into ketenes and ketene imines using PNN pincer complexes." Organic Chemistry Frontiers 2, no. 12 (2015): 1561–77. http://dx.doi.org/10.1039/c5qo00287g.

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10

Glessi, Cristiano, Aya Mahgoub, Cornelis W. Hagen, and Mats Tilset. "Gold(I) N-heterocyclic carbene precursors for focused electron beam-induced deposition." Beilstein Journal of Nanotechnology 12 (March 17, 2021): 257–69. http://dx.doi.org/10.3762/bjnano.12.21.

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Seven gold(I) N-heterocyclic carbene (NHC) complexes were synthesized, characterized, and identified as suitable precursors for focused electron beam-induced deposition (FEBID). Several variations on the core Au(NHC)X moiety were introduced, that is, variations of the NHC ring (imidazole or triazole), of the alkyl N-substituents (Me, Et, or iPr), and of the ancillary ligand X (Cl, Br, I, or CF3). The seven complexes were tested as FEBID precursors in an on-substrate custom setup. The effect of the substitutions on deposit composition and growth rate indicates that the most suitable organic ligand for the gold precursor is triazole-based, with the best deposit composition of 15 atom % gold, while the most suitable anionic ligand is the trifluoromethyl group, leading to a growth rate of 1 × 10−2 nm3/e−.

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11

Chen, Zhen, Yuwen Huo, Ping An, Xichao Wang, Chun Song, and Yudao Ma. "[2.2]Paracyclophane-based N-heterocyclic carbene as efficient catalyst or as ligand for copper catalyst for asymmetric α-silylation of N-tosylaldimines." Organic Chemistry Frontiers 3, no. 12 (2016): 1725–37. http://dx.doi.org/10.1039/c6qo00386a.

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12

Nishiura, Toshiki, Asako Takabatake, Mariko Okutsu, Jun Nakazawa, and Shiro Hikichi. "Heteroleptic cobalt(iii) acetylacetonato complexes with N-heterocyclic carbine-donating scorpionate ligands: synthesis, structural characterization and catalysis." Dalton Transactions 48, no. 8 (2019): 2564–68. http://dx.doi.org/10.1039/c8dt04469d.

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13

Rodriguez, Regina, Domenic Contrino, and David Mazyck. "Role of Activated Carbon Precursor for Mercury Oxidation and Removal: Oxidized Surface and Carbene Site Interaction." Processes 9, no. 7 (July 8, 2021): 1190. http://dx.doi.org/10.3390/pr9071190.

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Activated carbon (AC) is widely accepted for the removal of inorganic contaminants like mercury; however, the raw material used in the production of activated carbon is not always taken into consideration when evaluating its efficacy. Mercury oxidation and adsorption mechanisms governed by carbene sites are more likely to occur when graphitic-like activated carbons (such as those produced from high-ranking coals) are employed versus lignocellulosic-based ACs; this is likely due to the differences in carbon structures where lignocellulosic materials are less aromatic. In this research, the team studied bituminous coal-based ACs in comparison to coconut shell and wood-based (both less aromatic) ACs for elemental mercury removal. Nitric acid of 0.5 M, 1 M, and 5 M concentrations along with 10 M hydrogen peroxide were used to oxidize the surface of the ACs. Boehm titrations and FTIR analysis were used to quantify the addition of functional groups on the activated carbons. A trend was observed herein, resulting in increasing nitric acid molarity and an increased quantity of oxygen-containing functional groups. Gas-phase mercury removal mechanisms including physisorption, oxygen functional groups, and carbene sites were evaluated. The results showed significantly better elemental mercury removal in the gas phase with a bituminous coal-based AC embodying similar physical and chemical characteristics to that of its coconut shell-based counterpart. The ACs treated with various oxidizing agents to populate oxygen functional groups on the surface showed increased mercury removal. It is hypothesized that nitric acid treatment creates oxygen functional groups and carbene sites, with carbene sites being more responsible for mercury removal. Heat treatments post-oxidation with nitric acid showed remarkable results in mercury removal. This process created free carbene sites on the surface and shows that carbene sites are more reactive to mercury adsorption than oxygen. Overall, physisorption and oxygen functional groups were also dismissed as mercury removal mechanisms, leaving carbene-free sites as the most compelling mechanism.

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14

Guo, Jing, Yangbin Liu, Xiangqiang Li, Xiaohua Liu, Lili Lin, and Xiaoming Feng. "Nickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene." Chemical Science 7, no. 4 (2016): 2717–21. http://dx.doi.org/10.1039/c5sc03658e.

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15

Ren, Chao, Jingshu Zeng, and Gang Zou. "Nickel-catalyzed cross-coupling of O,N-chelated diarylborinates with aryl chlorides and mesylates." New Journal of Chemistry 43, no. 3 (2019): 1589–96. http://dx.doi.org/10.1039/c8nj05503c.

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Practical nickel catalysis for efficient cross-coupling of O,N-chelated diarylborinates with aryl chlorides and mesylates based on air-stable yet readily activated organonickel precursor, trans-NiCl(Ph)(PPh₃)₂, and sterically unsymmetrical N-heterocyclic carbene in situ generated from imidazolium precursor with trihydrate potassium phosphate in toluene.

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16

Melis, Karen, Dirk De Vos, Pierre Jacobs, and Francis Verpoort. "Acid controlled alkyne dimerisation initiated by a Ru–carbene precursor." Journal of Organometallic Chemistry 659, no. 1-2 (October 2002): 159–64. http://dx.doi.org/10.1016/s0022-328x(02)01722-9.

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17

Sureshbabu, Bemineni, Venkatachalam Ramkumar, and Sethuraman Sankararaman. "Facile base-free in situ generation and palladation of mesoionic and normal N-heterocyclic carbenes at ambient conditions." Dalton Trans. 43, no. 28 (2014): 10710–12. http://dx.doi.org/10.1039/c4dt01112k.

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18

Le, Nguyen Nhat Thu, Josefine Just, Jonathan M. Pankauski, Paul R. Rablen, and Dasan M. Thamattoor. "Ring Expansion of Alkylidenecarbenes Derived from Lactams, Lactones, and Thiolactones into Strained Heterocyclic Alkynes: A Theoretical Study." Molecules 24, no. 3 (February 7, 2019): 593. http://dx.doi.org/10.3390/molecules24030593.

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Strained cycloalkynes are of considerable interest to theoreticians and experimentalists, and possess much synthetic value as well. Herein, a series of cyclic alkylidenecarbenes—formally obtained by replacing the carbonyl oxygen of four-, five-, and six-membered lactams, lactones, and thiolactones with a divalent carbon—were modeled at the CCSD(T)/cc-pVTZ//B3LYP/6-311+G** and CCSD(T)/cc-pVTZ//CCSD/6-311+G** levels of theory. The singlet carbenes were found to be more stable than the triplets. The strained heterocyclic alkynes formed by ring expansion of these singlet carbenes were also modeled. Interestingly, the C≡C bonds in the five-membered heterocycles, obtained from the rearrangement of β-lactam- and β-lactone-derived alkylidenecarbenes, displayed lengths intermediate between formal double and triple bonds. Furthermore, 2-(1-azacyclobutylidene)carbene was found to be nearly isoenergetic with its ring-expanded isomer, and 1-oxacyclopent-2-yne was notably higher in energy than its precursor carbene. In all other cases, the cycloalkynes were lower in energy than the corresponding carbenes. The transition states for ring-expansion were always lower for the 1,2-carbon shifts than for 1,2-nitrogen or oxygen shifts, but higher than for the 1,2-sulfur shifts. These predictions should be verifiable using carbenes bearing appropriate isotopic labels. Computed vibrational spectra for the carbenes, and their ring-expanded isomers, are presented and could be of value to matrix isolation experiments.

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19

Boysen, Nils, Bujamin Misimi, Arbresha Muriqi, Jan-Lucas Wree, Tim Hasselmann, Detlef Rogalla, Tobias Haeger, et al. "A carbene stabilized precursor for the spatial atomic layer deposition of copper thin films." Chemical Communications 56, no. 89 (2020): 13752–55. http://dx.doi.org/10.1039/d0cc05781a.

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20

Ren, Demin, Sebastian Koniarz, Xiaofang Li, and Piotr J. Chmielewski. "First imidazole-fused carbaporphyrinoid and its conversion to a N-heterocyclic carbene precursor." Chemical Communications 56, no. 35 (2020): 4836–39. http://dx.doi.org/10.1039/d0cc01013h.

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21

Bendedouche, Choukri Kamel, and Hadj Benhaoua. "Copper-Exchanged Bentonite: A Reusable Catalysis for the Formation of Alkoxycarbonyl Nitrile Ylides under Microwave Irradiation." Journal of Chemical Research 36, no. 3 (March 2012): 149–51. http://dx.doi.org/10.3184/174751912x13298456741454.

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Ethyldiazoacetate reacts as a carbene precursor in presence of copper exchanged bentonite. Reaction with excess nitrile gave oxazole derivatives. Their formation is explained by intramolecular 1,5-cyclisation of alkoxycarbonyl substituted nitrile ylide intermediate.

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22

Li, Fang, Chao Pei, and Rene M. Koenigs. "Rhodium-Catalyzed Enamine Homologation of Sulfides with Triazoles as Carbene Precursor." Organic Letters 22, no. 17 (August 13, 2020): 6816–21. http://dx.doi.org/10.1021/acs.orglett.0c02330.

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23

Yao, Changguang, Hongyan Xie, and Dongmei Cui. "Highly 3,4-selective living polymerization of 2-phenyl-1,3-butadiene with amidino N-heterocyclic carbene ligated rare-earth metal bis(alkyl) complexes." RSC Advances 5, no. 113 (2015): 93507–12. http://dx.doi.org/10.1039/c5ra18713c.

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2-Phenyl-1,3-butadiene was polymerized using an amidino N-heterocyclic carbene lutetium bis(alkyl) precursor in high 3,4-selectivity (96.9%) and a living mode to afford a new plastic polydiene with a high T_g of 56.1 °C.

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24

Ren, Wei, Ming Jin, Qian-Ming Zuo, and Shang-Dong Yang. "Allylation of β-amino phosphonic acid precursor via palladium-NHC catalyzed allylic C–H activation." Organic Chemistry Frontiers 7, no. 2 (2020): 298–302. http://dx.doi.org/10.1039/c9qo01089k.

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A Pd(ii)/N-heterocyclic carbene (NHC) catalyzed allylic C–H alkylation of allylbenzene with α-cyano-phosphate ester has been achieved under mild reaction conditions with the highest regioselectivity and stereoselectivity.

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25

Seo, Ue Ryung, and Young Keun Chung. "Poly(4-vinylimidazolium) iodides: a highly recyclable organocatalyst precursor for benzoin condensation reaction." RSC Adv. 4, no. 61 (2014): 32371–74. http://dx.doi.org/10.1039/c4ra05073h.

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The development of highly efficient, recyclable poly(4-vinylimidazolium) iodides (2) for the benzoin condensation reaction under mild reaction conditions is discussed: poly(4-vinylN-heterocyclic carbene)s (3) obtained from2showed a higher catalytic activity and could be successfully recovered and reused over seven times without loss of performance.

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26

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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27

Liu, Xiang, Kaiqi Ge, Pei Guan, Pang He, Yunfei Li, Yanhui Shi, and Changsheng Cao. "Synthesis of anovel sterically hindered imidazolinium chloride: an N-heterocyclic carbene precursor." Journal of Chemical Research 36, no. 5 (May 1, 2012): 288–89. http://dx.doi.org/10.3184/174751912x13332884511554.

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28

Hildebrandt, Björn, and Christian Ganter. "Reactivity of a cationic N-heterocyclic carbene and its corresponding dicationic precursor." Journal of Organometallic Chemistry 717 (October 2012): 83–87. http://dx.doi.org/10.1016/j.jorganchem.2012.07.014.

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29

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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30

Li, Weiyi, Dongfeng Huang, and Yajing Lv. "Mechanism of N-heterocyclic carbene-catalyzed chemical fixation of CO2 with aziridines: a theoretical study." RSC Adv. 4, no. 33 (2014): 17236–44. http://dx.doi.org/10.1039/c4ra01018c.

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31

Doimeadios, Jorge. "Synthesis by self-assembly and structural characterization of a new co-crystal system {[Cu(NO3)2(H2O)2]L1(NO3)2} (L1 = 1,1′-dibenzyl-3,3′-butyl-diimidazolium-2,2′-diylidene) from copper nitrate and a carbene precursor." Open Chemistry 6, no. 4 (December 1, 2008): 505–8. http://dx.doi.org/10.2478/s11532-008-0062-z.

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AbstractHerein, the first example of a co-crystal system formed by an imidazolium nitrate, a carbene precursor, and copper (II) nitrate, {[Cu(NO3)2(H2O)2]L1(NO3)2} (1) (L1 = 1,1′-dibenzyl-3,3′-butyl-diimidazolium-2,2′-diylidene) is reported. These two building blocks are connected in the solid state through hydrogen bonds to generate a three-dimensional supramolecular network.

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32

Ringger, David H., and Peter Chen. "Rational Design of a Gold Carbene Precursor Complex for a Catalytic Cyclopropanation Reaction." Angewandte Chemie International Edition 52, no. 17 (March 25, 2013): 4686–89. http://dx.doi.org/10.1002/anie.201209569.

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33

Jung, Stefan, Kerstin Ilg, Justin Wolf, and Helmut Werner. "Cationic Vinyl and Dicationic Carbene Ruthenium(II) Complexes from a Vinylidene(hydrido) Precursor." Organometallics 20, no. 11 (May 2001): 2121–23. http://dx.doi.org/10.1021/om0100737.

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34

Wang, Jianbo, and Kang Wang. "Transition-Metal-Catalyzed Cross-Coupling with Non-Diazo Carbene Precursors." Synlett 30, no. 05 (October 16, 2018): 542–51. http://dx.doi.org/10.1055/s-0037-1611020.

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Transition-metal-catalyzed cross-coupling reactions through metal carbene migratory insertion have emerged as powerful methodology for carbon–carbon bond constructions. Typically, diazo compounds (or in situ generated diazo compounds from N-tosylhydrazones) have been employed as the metal carbene precursors for this type of cross-coupling reactions. Recently, cross-coupling reactions employing non-diazo carbene precursors, such as conjugated ene-yne-ketones, allenyl ketones, alkynes, cyclopropenes, and Cr(0) Fischer carbenes, have been developed. This account will summarize our efforts in the development of transition-metal-catalyzed cross-coupling reactions with these non-diazo carbene precursors.1 Introduction2 Cross-Coupling with Ene-yne-ketones, Allenyl Ketones, and Alkynes3 Cross-Coupling Involving Ring-Opening of Cyclopropenes4 Palladium-Catalyzed Cross-Coupling with Chromium(0) Fischer Carbenes5 Conclusion

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35

VAN DER MAELEN URÍA, JUAN F., JAVIER RUIZ, and SANTIAGO GARCÍA-GRANDA. "THEORETICAL CHARACTERIZATION OF A HIGHLY ELECTROPHILIC CARBENE." Journal of Theoretical and Computational Chemistry 04, no. 03 (September 2005): 823–32. http://dx.doi.org/10.1142/s0219633605001854.

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The experimental geometry obtained from single-crystal X-ray diffraction data for a metalladiphosphanyl carbene precursor is compared with the results of theoretical calculations made at the ab initio level by using Hartree–Fock (HF) and Density Functional Theory (DFT) methods over the carbene itself. Theoretical geometry optimizations for the singlet ground state of [ Mn(CO)4(PH2)2C: ]+ have been performed with several hybrid functionals and basis sets. Calculated geometries showed a perfect C 2v symmetry in the highest levels of calculation and were somewhat relaxed when compared with the experimental ones; for instance, with the largest basis set, the P–C–P angle found was 124.8°, whereas C–P bond distances were both 1.667 Å, compared to 103.5(3)° and 1.718(5) Å, respectively, from the experimental data. The absence of a ligand attached to the C : atom in the calculated structure, which is present in the form of iodine in the experimental complex, is probably responsible, to a certain extent, for the discrepancies. In addition to the structural computations, in order to theoretically quantify the highly electrophilic character expected for the carbene, electron affinities were calculated and found to be between 6.24 eV and 6.97 eV at different DFT levels of calculation, which confirmed the expectations. In this respect, a comparison with the analogous [Ru(CNH)4(PH2)2C:]2+ carbene is also made, showing the possibility of experimentally trapping the manganese carbene.

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36

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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37

Bobek, Michael M., Gerald Giester, Hanspeter Kählig, and Udo H. Brinker. "A ‘sugar-coated’ carbene precursor: a single crystal X-ray diffraction and NMR study." Tetrahedron Letters 41, no. 30 (July 2000): 5663–67. http://dx.doi.org/10.1016/s0040-4039(00)00938-2.

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38

Troschke, Erik, Khoa Dang Nguyen, Silvia Paasch, Johannes Schmidt, Georg Nickerl, Irena Senkovska, Eike Brunner, and Stefan Kaskel. "Integration of an N‐Heterocyclic Carbene Precursor into a Covalent Triazine Framework for Organocatalysis." Chemistry – A European Journal 24, no. 70 (November 20, 2018): 18629–33. http://dx.doi.org/10.1002/chem.201804373.

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39

Toerien, James G., Mieke Desmet, Gert J. Kruger, and Helgard G. Raubenheimer. "Carbene complexes of FeII prepared from a precursor complex containing a remote nucleophilic heteroatom." Journal of Organometallic Chemistry 479, no. 1-2 (October 1994): c12—c15. http://dx.doi.org/10.1016/0022-328x(94)84119-5.

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40

Wagner, Hannah K., Hubert Wadepohl, and Joachim Ballmann. "A 2,2′-diphosphinotolane as a versatile precursor for the synthesis of P-ylidic mesoionic carbenes via reversible C–P bond formation." Chemical Science 12, no. 10 (2021): 3693–701. http://dx.doi.org/10.1039/d0sc06128j.

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A metal-templated synthesis of cyclic (aryl)(ylidic)mesoionic carbene complexes (CArY-MICs) is presented. In the case of molybdenum carbonyls, the crucial P–C bond formation, which occurs during CArY-MIC formation, was found to be reversible.

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41

Xu, Youwei, Xukai Zhou, Guangfan Zheng, and Xingwei Li. "Sulfoxonium Ylides as a Carbene Precursor in Rh(III)-Catalyzed C–H Acylmethylation of Arenes." Organic Letters 19, no. 19 (September 13, 2017): 5256–59. http://dx.doi.org/10.1021/acs.orglett.7b02531.

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42

Camacho, Margaret B., Aurora E. Clark, Tabitha A. Liebrecht, and JoAnn P. DeLuca. "A Phenyliodonium Ylide as a Precursor for Dicarboethoxycarbene: Demonstration of a Strategy for Carbene Generation." Journal of the American Chemical Society 122, no. 21 (May 2000): 5210–11. http://dx.doi.org/10.1021/ja000334o.

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43

Chi, Le Thi Loan, Agus Suharto, Ho Linh Da, Soda Chanthamath, Kazutaka Shibatomi, and Seiji Iwasa. "Catalytic Asymmetric Intermolecular Cyclopropanation of a Ketone Carbene Precursor by a Ruthenium(II)-Pheox Complex." Advanced Synthesis & Catalysis 361, no. 5 (January 17, 2019): 951–55. http://dx.doi.org/10.1002/adsc.201801077.

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44

Liu, Xiang, Kaiqi Ge, Pei Guan, Pang He, Yunfei Li, Yanhui Shi, and Changsheng Cao. "ChemInform Abstract: Synthesis of a Novel Sterically Hindered Imidazolinium Chloride: An N-Heterocyclic Carbene Precursor." ChemInform 43, no. 42 (September 20, 2012): no. http://dx.doi.org/10.1002/chin.201242126.

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45

Zhu, Shi-Zheng, and Qing-Yun Chen. "Phenyliodonium bis(perfluoroalkane sulphonyl) methide; synthesis and reactions as a precursor of bis(perfluoroalkanesulphonyl) carbene." Journal of the Chemical Society, Chemical Communications, no. 20 (1990): 1459. http://dx.doi.org/10.1039/c39900001459.

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46

Silva, Rodolpho A. N., Patrícia Borim, Larissa R. Fonseca, Benedito S. Lima-Neto, José L. Silva Sá, and Valdemiro P. Carvalho-Jr. "Non-carbene Complex [RuCl2(PPh3)2(azocane)] as Active Catalyst Precursor for ROMP and ATRP." Catalysis Letters 147, no. 5 (March 9, 2017): 1144–52. http://dx.doi.org/10.1007/s10562-017-2003-y.

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47

Hemming, Ellen B., Anthony F. Masters, and Thomas Maschmeyer. "Immobilisation of Homogeneous Pd Catalysts within a Type I Porous Liquid." Australian Journal of Chemistry 73, no. 12 (2020): 1296. http://dx.doi.org/10.1071/ch20256.

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An N-heterocyclic carbene-based palladium complex was successfully immobilised on the inner surfaces of hollow silica nanospheres. The external surfaces of these spheres were functionalised with a corona-canopy to produce a Type I porous liquid. To confirm the successful immobilisation of the catalytic precursor, the porous liquid system was explored using the Heck reaction as a model reaction. This work demonstrated that homogeneous catalysts can be successfully immobilised within porous liquids in principle and that the approach used could be readily adapted for the immobilisation of other systems.

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48

Coyle, Jason P., Gangotri Dey, Eric R. Sirianni, Marianna L. Kemell, Glenn P. A. Yap, Mikko Ritala, Markku Leskelä, Simon D. Elliott, and Sean T. Barry. "Deposition of Copper by Plasma-Enhanced Atomic Layer Deposition Using a Novel N-Heterocyclic Carbene Precursor." Chemistry of Materials 25, no. 7 (March 29, 2013): 1132–38. http://dx.doi.org/10.1021/cm400215q.

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49

Palencia, Hector, Federico Garcia-Jimenez, and James M. Takacs. "Suzuki–Miyaura coupling with high turnover number using an N-acyl-N-heterocyclic carbene palladacycle precursor." Tetrahedron Letters 45, no. 20 (May 2004): 3849–53. http://dx.doi.org/10.1016/j.tetlet.2004.03.138.

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ZHU, S. Z., and Q. Y. CHEN. "ChemInform Abstract: Phenyliodonium Bis(perfluoroalkanesulfonyl) Methide. Synthesis and Reactions as a Precursor of Bis(perfluoroalkanesulfonyl)carbene." ChemInform 22, no. 14 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199114115.

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