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Journal articles on the topic 'Palladium - N - heterocyclic carbene'

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Author: Grafiati

Published: 18 May 2024

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1

Feng, Can, Cheng-xin Liu, Yu-fang Wang, Jin Cui, and Ming-jie Zhang. "Synthesis and characterization of a new bis-NHC palladium complex and its catalytic activity in the Mizoroki–Heck reaction." Journal of Chemical Research 44, no. 11-12 (May 14, 2020): 684–88. http://dx.doi.org/10.1177/1747519820917883.

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A new bis- N-heterocyclic carbene palladium complex, (C13H9N2F2)2PdCl2, is synthesized by a three-step reaction and characterized by 1H NMR and 13C NMR spectroscopy as well as by X-ray crystallography. This new bis- N-heterocyclic carbene palladium complex has excellent stability and is capable of efficiently catalyzing the Mizoroki–Heck coupling reaction of aryl halides with acrylates.

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2

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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3

Sprengers, Jeroen W., Jeroen Wassenaar, Nicolas D. Clement, Kingsley J. Cavell, and Cornelis J. Elsevier. "Palladium-(N-Heterocyclic Carbene) Hydrogenation Catalysts." Angewandte Chemie International Edition 44, no. 13 (March 18, 2005): 2026–29. http://dx.doi.org/10.1002/anie.200462930.

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4

Sprengers, Jeroen W., Jeroen Wassenaar, Nicolas D. Clement, Kingsley J. Cavell, and Cornelis J. Elsevier. "Palladium-(N-Heterocyclic Carbene) Hydrogenation Catalysts." Angewandte Chemie 117, no. 13 (March 18, 2005): 2062–65. http://dx.doi.org/10.1002/ange.200462930.

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5

Xu, Lijin, Weiping Chen, Jamie F. Bickley, Alexander Steiner, and Jianliang Xiao. "Fluoroalkylated N-heterocyclic carbene complexes of palladium." Journal of Organometallic Chemistry 598, no. 2 (April 2000): 409–16. http://dx.doi.org/10.1016/s0022-328x(00)00008-5.

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6

Bergbreiter, David E., Haw-Lih Su, Hisao Koizumi, and Jianhua Tian. "Polyisobutylene-supported N-heterocyclic carbene palladium catalysts." Journal of Organometallic Chemistry 696, no. 6 (March 2011): 1272–79. http://dx.doi.org/10.1016/j.jorganchem.2010.10.058.

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7

Li, Jianxiao, Can Li, Lu Ouyang, Chunsheng Li, Wanqing Wu, and Huanfeng Jiang. "N-Heterocyclic carbene palladium-catalyzed cascade annulation/alkynylation of 2-alkynylanilines with terminal alkynes." Organic & Biomolecular Chemistry 15, no. 37 (2017): 7898–908. http://dx.doi.org/10.1039/c7ob01889d.

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8

Wang, Tao, Lantao Liu, Kai Xu, Huanping Xie, Hui Shen, and Wen-Xian Zhao. "Synthesis and characterization of trinuclear N-heterocyclic carbene–palladium(ii) complexes and their applications in the Suzuki–Miyaura cross-coupling reaction." RSC Advances 6, no. 103 (2016): 100690–95. http://dx.doi.org/10.1039/c6ra20852e.

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Five novel trinuclear N-heterocyclic carbene–palladium(ii) complexes 5a–e were conveniently synthesized in one step. The obtained palladium(ii) complexes were the effective catalyst precursors for the Suzuki–Miyaura coupling.

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9

Abdellah, Ibrahim, Pauline Kasongo, Axel Labattut, Régis Guillot, Emmanuelle Schulz, Cyril Martini, and Vincent Huc. "Benzyloxycalix[8]arene: a new valuable support for NHC palladium complexes in C–C Suzuki–Miyaura couplings." Dalton Transactions 47, no. 39 (2018): 13843–48. http://dx.doi.org/10.1039/c8dt02550a.

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10

Steeples, Elliot, Alexandra Kelling, Uwe Schilde, and Davide Esposito. "Amino acid-derived N-heterocyclic carbene palladium complexes for aqueous phase Suzuki–Miyaura couplings." New Journal of Chemistry 40, no. 6 (2016): 4922–30. http://dx.doi.org/10.1039/c5nj03337c.

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11

Meyer, Dirk, and Thomas Strassner. "Methylpalladium complexes with pyrimidine-functionalized N-heterocyclic carbene ligands." Beilstein Journal of Organic Chemistry 12 (July 21, 2016): 1557–65. http://dx.doi.org/10.3762/bjoc.12.150.

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A series of methylpalladium(II) complexes with pyrimidine-NHC ligands carrying different aryl- and alkyl substituents R ([((pym)^(NHC-R))PdII(CH3)X] with X = Cl, CF3COO, CH3) has been prepared by transmetalation reactions from the corresponding silver complexes and chloro(methyl)(cyclooctadiene)palladium(II). The dimethyl(1-(2-pyrimidyl)-3-(2,6-diisopropylphenyl)imidazolin-2-ylidene)palladium(II) complex was synthesized via the free carbene route. All complexes were fully characterized by standard methods and in three cases also by a solid state structure.

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12

Therrien, J. A., M. O. Wolf, and B. O. Patrick. "Synthesis and comparison of nickel, palladium, and platinum bis(N-heterocyclic carbene) pincer complexes for electrocatalytic CO2 reduction." Dalton Transactions 47, no. 6 (2018): 1827–40. http://dx.doi.org/10.1039/c7dt04089j.

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13

Zhang, Fei-Yi, Xiao-Bing Lan, Chang Xu, Hua-Gang Yao, Tian Li, and Feng-Shou Liu. "Rigid hindered N-heterocyclic carbene palladium precatalysts: synthesis, characterization and catalytic amination." Organic Chemistry Frontiers 6, no. 18 (2019): 3292–99. http://dx.doi.org/10.1039/c9qo00726a.

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Rigid hindered N-heterocyclic carbene palladium complexes have been developed and exhibited high activities for a variety of (hetero)aryl chlorides with (hetero)anilines and amines under aerobic conditions.

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14

Purohit, Vishal B., Sharad C. Karad, Kirit H. Patel, and Dipak K. Raval. "Palladium N-heterocyclic carbene catalyzed regioselective C–H halogenation of 1-aryl-3-methyl-1H-pyrazol-5(4H)-ones using N-halosuccinimides (NXS)." Catalysis Science & Technology 5, no. 6 (2015): 3113–18. http://dx.doi.org/10.1039/c5cy00137d.

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A novel palladium N-heterocyclic carbene complex of vitamin B₁ was prepared and employed for regioselective C–H halogenation of 1-aryl-3-methyl-1H-pyrazol-5(4H)-ones using N-halosuccinimides.

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15

Wang, Tao, Jiarui Guo, Xiaojuan Wang, Han Guo, Dingli Jia, Hengjin Wang, and Lantao Liu. "Cross coupling of benzylammonium salts with boronic acids using a well-defined N-heterocyclic carbene–palladium(ii) precatalyst." RSC Advances 9, no. 10 (2019): 5738–41. http://dx.doi.org/10.1039/c8ra10439e.

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16

Tegeder, Patricia, Marcello Marelli, Matthias Freitag, Laura Polito, Sebastian Lamping, Rinaldo Psaro, Frank Glorius, Bart Jan Ravoo, and Claudio Evangelisti. "Metal vapor synthesis of ultrasmall Pd nanoparticles functionalized with N-heterocyclic carbenes." Dalton Transactions 47, no. 36 (2018): 12647–51. http://dx.doi.org/10.1039/c8dt02535e.

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The synthesis of N-heterocyclic carbene (NHC)-stabilized palladium nanoparticles (PdNPs) by an entirely new strategy comprising the NHC functionalization of ligand-free PdNPs obtained by metal vapor synthesis is described.

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17

Zhao, Huaixia, Liuyi Li, Jinyun Wang, and Ruihu Wang. "Spherical core–shell magnetic particles constructed by main-chain palladium N-heterocyclic carbenes." Nanoscale 7, no. 8 (2015): 3532–38. http://dx.doi.org/10.1039/c4nr07330d.

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18

Tulloch, Arran A. D., Andreas A. Danopoulos, Sean M. Cafferkey, Sven Kleinhenz, Michael B. Hursthouse, and Robert P. Tooze. "Pyridine functionalised N-heterocyclic carbene complexes of palladium." Chemical Communications, no. 14 (2000): 1247–48. http://dx.doi.org/10.1039/b002645j.

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19

Liu, Kun, M. Todd Hovey, and Karl A. Scheidt. "A cooperative N-heterocyclic carbene/palladium catalysis system." Chemical Science 5, no. 10 (July 23, 2014): 4026. http://dx.doi.org/10.1039/c4sc01536c.

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20

Nagai, Yusuke, Takuya Kochi, and Kyoko Nozaki. "Synthesis of N-Heterocyclic Carbene-Sulfonate Palladium Complexes." Organometallics 28, no. 20 (October 26, 2009): 6131–34. http://dx.doi.org/10.1021/om9004252.

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21

Liu, Ji-Quan, Xing-Xing Gou, and Ying-Feng Han. "Chelating Bis(N-Heterocyclic Carbene) Palladium-Catalyzed Reactions." Chemistry - An Asian Journal 13, no. 17 (July 30, 2018): 2257–76. http://dx.doi.org/10.1002/asia.201800583.

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22

Prajapati, D., C. Schulzke, M. K. Kindermann, and A. R. Kapdi. "Selective palladium-catalysed arylation of 2,6-dibromopyridine using N-heterocyclic carbene ligands." RSC Advances 5, no. 65 (2015): 53073–85. http://dx.doi.org/10.1039/c5ra10561g.

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A selective palladium-catalysed arylation of 2,6-dibromopyridine has been developed by employing N-heterocyclic carbene ligands. Selective mono-arylation was performed in water/acetonitrile solvent at ambient temperature and low catalyst loading.

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23

Zhao, Xiao-Yun, Quan Zhou, and Jian-Mei Lu. "Synthesis and characterization of N-heterocyclic carbene-palladium(ii) chlorides-1-methylindazole and -1-methylpyrazole complexes and their catalytic activity toward C–N coupling of aryl chlorides." RSC Advances 6, no. 29 (2016): 24484–90. http://dx.doi.org/10.1039/c6ra02556k.

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N-heterocyclic carbene-palladium(ii) chlorides-1-methylindazole and -1-methylpyrazole complexes were successfully synthesized and characterized. Investigations showed that they were efficient catalysts in amine coupling with aryl chlorides at low catalyst loadings.

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24

Crawford, Katherine A., Alan H. Cowley, and Simon M. Humphrey. "Bis(imino)acenaphthene (BIAN)-supported palladium(ii) carbene complexes as effective C–C coupling catalysts and solvent effects in organic and aqueous media." Catal. Sci. Technol. 4, no. 5 (2014): 1456–64. http://dx.doi.org/10.1039/c4cy00192c.

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25

Nahra, Fady, and Catherine S. J. Cazin. "Sustainability in Ru- and Pd-based catalytic systems using N-heterocyclic carbenes as ligands." Chemical Society Reviews 50, no. 5 (2021): 3094–142. http://dx.doi.org/10.1039/c8cs00836a.

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This review is a critical presentation of catalysts based on palladium and ruthenium bearing N-heterocyclic carbene ligands that have enabled a more sustainable approach to catalysis and to catalyst uses.

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26

Hillier, Anna C., and Steven P. Nolan. "Palladium/Nucleophilic Carbene Catalysts for Cross-Coupling Reactions." Platinum Metals Review 46, no. 2 (April 1, 2002): 50–64. http://dx.doi.org/10.1595/003214002x4625064.

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Palladium complexes bearing N-heterocyclic nucleophilic carbenes can function as efficient and convenient mediators of C-C and C-N cross-coupling reactions. These phosphine-free systems are highly effective in coupling reactions of aryl bromides and aryl chlorides with a variety of coupling partners. Some applications of these Palladium complexes in a range of coupling reactions are described here and catalysts, conditions and results are presented.

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27

Zinser, Caroline M., Fady Nahra, Marcel Brill, Rebecca E. Meadows, David B. Cordes, Alexandra M. Z. Slawin, Steven P. Nolan, and Catherine S. J. Cazin. "A simple synthetic entryway into palladium cross-coupling catalysis." Chemical Communications 53, no. 57 (2017): 7990–93. http://dx.doi.org/10.1039/c7cc02487h.

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The simple synthesis of a family of palladates containing an imidazolium counterion is presented. These “ate” complexes can be easily converted into well-defined palladium–N-heterocyclic carbene (NHC) complexes.

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28

Bi, Weiyang, Yunhui Yang, Song Ye, and Congyang Wang. "Umpolung coupling of pyridine-2-carboxaldehydes and propargylic carbonates via N-heterocyclic carbene/palladium synergetic catalysis." Chemical Communications 57, no. 36 (2021): 4452–55. http://dx.doi.org/10.1039/d1cc01311d.

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The umpolung cross-coupling reaction of pyridine-2-carboxaldehydes and propargylic carbonates has been developed for the first time through N-heterocyclic carbene/palladium cooperative catalysis, giving the propargylic ketones regioselectively.

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29

Al Nasr, Ibrahim, Nedra Touj, Waleed Koko, Tariq Khan, Ismail Özdemir, Sedat Yaşar, and Naceur Hamdi. "Biological Activities of NHC–Pd(II) Complexes Based on Benzimidazolylidene N-heterocyclic Carbene (NHC) Ligands Bearing Aryl Substituents." Catalysts 10, no. 10 (October 15, 2020): 1190. http://dx.doi.org/10.3390/catal10101190.

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N-heterocyclic carbene (NHC) precursors (2a–i), their pyridine-enhanced precatalyst preparation stabilization and initiation (PEPPSI)-themed palladium N-heterocyclic carbene complexes (3a–i) and palladium N-heterocyclic triphenylphosphines complexes (4a–i) were synthesized and characterized by elemental analysis and 1H NMR, 13C NMR, IR, and LC–MS spectroscopic techniques. The (NHC)Pd(II) complexes 3–4 were tested against MCF7 and MDA-MB-231 cancer cells, Escherichia coli, methicillin-resistant Staphylococcus aureus (MRSA), Candida albicans microorganisms, Leishmania major promastigotes and amastigotes, Toxoplasma gondii parasites, and Vero cells in vitro. The biological assays indicated that all compounds are highly active against cancer cells, with an IC50 < 1.5 µg mL−1. Eight compounds proved antibacterial and antileishmanial activities, while only three compounds had strong antifungal activities against C. albicans. In our conclusion, compounds 3 (b, f, g, and h) and 4b are the most suitable drug candidates for anticancer, antimicrobial, and antiparasitical.

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30

Shimizu, Minori, Yuta Okuda, Koki Toyoda, Ryo Akiyama, Hiraku Shinozaki, and Tetsuya Yamamoto. "Pd-catalyzed synthesis of 1-(hetero)aryl-2,2,2-trichloroethanols using chloral hydrate and (hetero)arylboroxines." RSC Advances 11, no. 29 (2021): 17734–39. http://dx.doi.org/10.1039/d1ra02403e.

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N-heterocyclic carbene (NHC)-coordinated cyclometallated palladium complex (CYP) catalyzed (hetero)aryl addition of chloral hydrate using (hetero)arylboroxines, providing a new approach to 1-(hetero)aryl-2,2,2-trichloroethanols.

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31

Tao, W., S. Akita, R. Nakano, S. Ito, Y. Hoshimoto, S. Ogoshi, and K. Nozaki. "Copolymerisation of ethylene with polar monomers by using palladium catalysts bearing an N-heterocyclic carbene–phosphine oxide bidentate ligand." Chemical Communications 53, no. 17 (2017): 2630–33. http://dx.doi.org/10.1039/c7cc00002b.

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We report the synthesis and characterisation of palladium complexes bearing an N-heterocyclic carbene–phosphine oxide bidentate ligand and their use as catalysts for ethylene polymerisation and ethylene/polar monomer copolymerisation.

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32

Purohit, Vishal B., Sharad C. Karad, Kirit H. Patel, and Dipak K. Raval. "Palladium N-heterocyclic carbene catalyzed expected and unexpected C–C and C–N functionalization reactions of 1-aryl-3-methyl-1H-pyrazol-5(4H)-ones." RSC Advances 6, no. 112 (2016): 111139–43. http://dx.doi.org/10.1039/c6ra22779a.

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A palladium N-heterocyclic carbene complex of vitamin B₁ developed earlier in our laboratory was successfully employed as an efficient catalyst for the regioselective C–C and C–N functionalization reactions of 1-aryl-3-methyl-1H-pyrazol-5(4H)-ones.

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33

Jia, Yanyan, Tuanjie Li, Chenxia Yu, Bo Jiang, and Changsheng Yao. "A facile one-pot synthesis of 2,3-diarylated benzo[b]furans via relay NHC and palladium catalysis." Organic & Biomolecular Chemistry 14, no. 6 (2016): 1982–87. http://dx.doi.org/10.1039/c5ob02336j.

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An efficient one-pot synthesis of 2,3-diarylated benzo[b]furans was realized through the relay catalysis of N-Heterocyclic Carbene (NHC) and palladium from substituted 2′-bromodiphenylbromomethanes and aryl aldehydes.

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34

Lee, Jhen-Yi, Jiun-Shian Shen, Ru-Jiun Tzeng, I.-Chen Lu, Jenn-Huei Lii, Ching-Han Hu, and Hon Man Lee. "Well-defined palladium(0) complexes bearing N-heterocyclic carbene and phosphine moieties: efficient catalytic applications in the Mizoroki–Heck reaction and direct C–H functionalization." Dalton Transactions 45, no. 25 (2016): 10375–88. http://dx.doi.org/10.1039/c6dt01323f.

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A well-defined palladium(0) complex with a phosphine-functionalized N-heterocyclic carbene ligand was prepared and shown to be inefficient in catalyzing Mizoroki–Heck coupling and direct C–H functionalization reactions.

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35

Karthik, Shanmugam, and Thirumanavelan Gandhi. "Dibenzofuran and dibenzothiophene based palladium(ii)/NHC catalysts – synthesis and applications in C–C bond formation." New Journal of Chemistry 42, no. 19 (2018): 15811–19. http://dx.doi.org/10.1039/c8nj02989j.

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In the quest for a new ligand system for Pd(ii)/NHCs, we developed new dibenzofuran and dibenzothiophene based palladium N-heterocyclic carbene catalystsD1–D6in good yields and applied it in C–C bond formation.

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36

Vanden Broeck, Sofie M. P., Fady Nahra, and Catherine S. J. Cazin. "Bulky-Yet-Flexible Carbene Ligands and Their Use in Palladium Cross-Coupling." Inorganics 7, no. 6 (June 21, 2019): 78. http://dx.doi.org/10.3390/inorganics7060078.

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

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37

Blakemore, James D., Matthew J. Chalkley, Joy H. Farnaby, Louise M. Guard, Nilay Hazari, Christopher D. Incarvito, Eddie D. Luzik, and Hee Won Suh. "New BidentateTrans-Chelating N-Heterocyclic Carbene Ligands for Palladium." Organometallics 30, no. 7 (April 11, 2011): 1818–29. http://dx.doi.org/10.1021/om100890q.

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38

Guo, Chang, Mirco Fleige, Daniel Janssen-Müller, Constantin G. Daniliuc, and Frank Glorius. "Cooperative N-Heterocyclic Carbene/Palladium-Catalyzed Enantioselective Umpolung Annulations." Journal of the American Chemical Society 138, no. 25 (June 15, 2016): 7840–43. http://dx.doi.org/10.1021/jacs.6b04364.

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39

Tandukar, Shikchya, and Ayusman Sen. "N-heterocyclic carbene–palladium complex immobilized on silica nanoparticles." Journal of Molecular Catalysis A: Chemical 268, no. 1-2 (May 2007): 112–19. http://dx.doi.org/10.1016/j.molcata.2006.12.003.

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40

Liu, Yu, Rakesh Ganguly, Han Vinh Huynh, and Weng Kee Leong. "Palladium–Osmium Heterometallic Clusters Containing N-Heterocyclic Carbene Ligands." Organometallics 32, no. 24 (November 27, 2013): 7559–63. http://dx.doi.org/10.1021/om401031h.

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41

Mohammed H.S. Al-Jibori, Nabeel H. Buttrus, and Ahmed S.M. Al-Janabi. "Synthesis and Studies Pd(II)-NHC complexes with thiosaccharinate, saccharinate or benzothiazolinate ligands." Tikrit Journal of Pure Science 22, no. 2 (January 21, 2023): 99–103. http://dx.doi.org/10.25130/tjps.v22i2.633.

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Three cis-chelating di-N-heterocyclic carbene palladium(II) complexes [Pd(X)2(di- NHC)] (X= tsac, sac and bit) tsac= thiosaccharinate, sac= saccharinate, bit= benzisothiazolinate, bearing different anionic co-ligand was synthesized and characterized. A series of palladium(II) complexes (2-5) bearing cis-chelating homo-dicarbene ligand with varying propylene-bridged (C3) and N-heterocyclic backbones (imidazole) have been synthesized by reaction of [Pd(OAc)2] with the respective diazolium bromides in DMSO, have been prepared and characterized by elemental analysis, infrared spectra and 1H NMR. These compounds are all stabilized in the sold state. The bidentate (diNHC) ligand together with two N-coordenated sac , bit and two S-coordenated tsac ligand, from the square planar coordination geometry around the palladium(II) ion.

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42

Yang, Jin, Pinhua Li, Yicheng Zhang, and Lei Wang. "Dinuclear NHC–palladium complexes containing phosphine spacers: synthesis, X-ray structures and their catalytic activities towards the Hiyama coupling reaction." Dalton Trans. 43, no. 19 (2014): 7166–75. http://dx.doi.org/10.1039/c4dt00180j.

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Six dinuclear N-heterocyclic carbene–palladium complexes were synthesized from [Pd(μ-Cl)(Cl)(NHC)]₂ and Ph₂P(CH₂)_nPPh₂, and their catalytic activities towards the Hiyama reaction were investigated.

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43

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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44

Tubaro, Cristina, Marco Baron, Andrea Biffis, and Marino Basato. "Alkyne hydroarylation with Au N-heterocyclic carbene catalysts." Beilstein Journal of Organic Chemistry 9 (February 5, 2013): 246–53. http://dx.doi.org/10.3762/bjoc.9.29.

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Mono- and dinuclear gold complexes with N-heterocyclic carbene (NHC) ligands have been employed as catalysts in the intermolecular hydroarylation of alkynes with simple unfunctionalised arenes. Both mono- and dinuclear gold(III) complexes were able to catalyze the reaction; however, the best results were obtained with the mononuclear gold(I) complex IPrAuCl. This complex, activated with one equivalent of silver tetrafluoroborate, exhibited under acidic conditions at room temperature much higher catalytic activity and selectivity compared to more commonly employed palladium(II) catalysts. Moreover, the complex was active, albeit to a minor extent, even under neutral conditions, and exhibited lower activity but higher selectivity compared to the previously published complex AuCl(PPh3). Preliminary results on intramolecular hydroarylations using this catalytic system indicate, however, that alkyne hydration by traces of water may become a serious competing reaction.

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45

Wheaton, Craig A., and Mark Stradiotto. "Probing the utility of palladium complexes supported by morpholine-functionalized N-heterocyclic carbene ligands in Buchwald–Hartwig amination." Canadian Journal of Chemistry 91, no. 8 (August 2013): 755–62. http://dx.doi.org/10.1139/cjc-2013-0132.

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Convenient and high-yielding syntheses of two new morpholine-substituted N-heterocyclic carbene ligands, 1-Ar-3-{2-(4-morpholinyl)phenyl}imidazolidin-2-ylidene (Ar = Dipp, Mes), are described. An investigation of corresponding palladium complexes reveals hemilability, and examples of both monodentate and bidentate coordination are observed. A preliminary investigation of the activity of these palladium complexes for Buchwald–Hartwig amination catalysis is presented.

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46

Zende, V. M., C. Schulzke, and A. R. Kapdi. "Pincer CNC bis-N-heterocyclic carbenes: robust ligands for palladium-catalysed Suzuki–Miyaura arylation of bromoanthracene and related substrates." Organic Chemistry Frontiers 2, no. 10 (2015): 1397–410. http://dx.doi.org/10.1039/c5qo00236b.

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Novel pincer-type N-heterocyclic carbene ligands have been synthesised and characterised by FAB-MS and single crystal X-ray analysis. The ligands have proved to be highly active towards palladium-catalysed Suzuki–Miyaura cross-coupling of bromoanthracene and related substrates.

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47

Kandathil, Vishal, Bradley D. Fahlman, B. S. Sasidhar, Shivaputra A. Patil, and Siddappa A. Patil. "A convenient, efficient and reusable N-heterocyclic carbene-palladium(ii) based catalyst supported on magnetite for Suzuki–Miyaura and Mizoroki–Heck cross-coupling reactions." New Journal of Chemistry 41, no. 17 (2017): 9531–45. http://dx.doi.org/10.1039/c7nj01876b.

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In the present work, a new magnetic nanoparticle supported N-heterocyclic carbene-palladium(ii) (NO₂-NHC-Pd@Fe₃O₄) nanomagnetic catalyst was synthesized by a facile multistep synthesis under aerobic conditions.

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48

HERRMANN, W. A., C. P. REISINGER, and M. SPIEGLER. "ChemInform Abstract: N-Heterocyclic Carbenes. Part 17. Chelating N-Heterocyclic Carbene Ligands in Palladium-Catalyzed Heck-Type Reactions." ChemInform 29, no. 38 (June 19, 2010): no. http://dx.doi.org/10.1002/chin.199838060.

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49

Ghosh, Koena, Shubhajit Dhara, Sourav Jana, Subhomoy Das, and Sudeshna Roy. "NHC stabilized Pd nanoclusters in the Mizoroki–Heck reaction within microemulsion: exploring the role of imidazolium salt in rate enhancement." New Journal of Chemistry 43, no. 4 (2019): 1993–2001. http://dx.doi.org/10.1039/c8nj05118f.

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Significant rate enhancement of the Mizoroki–Heck reaction by in situ generated palladium nanoclusters within the confined space of water-in-oil mixed microemulsion in the presence of novel imidazo[1,5-α]pyridinium chlorides as N-heterocyclic carbene (NHC) precursors is reported.

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50

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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