N-Heterocyclic carbene–palladium(II)-1-methylimidazole complex catalyzed Mizoroki–Heck reaction of aryl chlorides with styrenes

Ting-Ting Gao, Ai-Ping Jin and Li-Xiong Shao
Beilstein J. Org. Chem. 2012, 8, 1916–1919. https://doi.org/10.3762/bjoc.8.222

Supporting Information

Supporting Information File 1: General procedure for the NHC-Pd(II)-Im complex 1 catalyzed Mizoroki–Heck reaction, characterization data and copies of spectra.
Format: PDF Size: 1.3 MB Download

Cite the Following Article

N-Heterocyclic carbene–palladium(II)-1-methylimidazole complex catalyzed Mizoroki–Heck reaction of aryl chlorides with styrenes
Ting-Ting Gao, Ai-Ping Jin and Li-Xiong Shao
Beilstein J. Org. Chem. 2012, 8, 1916–1919. https://doi.org/10.3762/bjoc.8.222

How to Cite

Gao, T.-T.; Jin, A.-P.; Shao, L.-X. Beilstein J. Org. Chem. 2012, 8, 1916–1919. doi:10.3762/bjoc.8.222

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Lerch, S.; Fritsch, S.; Strassner, T. The Mizoroki‐Heck Reaction in Tunable Aryl Alkyl Ionic Liquids. European Journal of Organic Chemistry 2022, 2022. doi:10.1002/ejoc.202200008
  • Zhang, Z.-M.; Xu, Y.-T.; Shao, L.-X. Synthesis of N-heterocyclic carbene-Pd(II)-5-phenyloxazole complexes and initial studies of their catalytic activity toward the Buchwald-Hartwig amination of aryl chlorides. Journal of Organometallic Chemistry 2021, 940, 121683. doi:10.1016/j.jorganchem.2021.121683
  • Ahmad, H. Celluloses as Green Support of Palladium Nanoparticles for Application in Heterogeneous Catalysis: A Brief Review. Journal of Cluster Science 2021, 33, 421–438. doi:10.1007/s10876-021-02000-z
  • Ahmad, H. Celluloses as Green Support of Palladium Nanoparticles for Application in Heterogeneous Catalysis: A Brief Review. Journal of Cluster Science 2021, 1–18.
  • Islam, M. S.; Nahra, F.; Tzouras, N. V.; Barakat, A.; Cazin, C. S. J.; Nolan, S. P.; Al-Majid, A. M. Mizoroki-Heck cross-coupling of acrylate derivatives with aryl halides catalyzed by palladate pre-catalysts. European Journal of Inorganic Chemistry 2019, 2019, 4695–4699. doi:10.1002/ejic.201901075
  • Schroeter, F.; Strassner, T. Understanding Anionic "Ligandless" Palladium Species in the Mizoroki-Heck Reaction. Inorganic chemistry 2018, 57, 5159–5173. doi:10.1021/acs.inorgchem.8b00175
  • Sun, K.-X.; He, Q.-W.; Xu, B.-B.; Wu, X.-T.; Lu, J.-M. Synthesis of N‐Heterocyclic Carbene–PdII–2‐Methyl‐4,5‐dihydrooxazole Complexes and Their Application Toward Highly Chemoselective Mono‐Suzuki–Miyaura Coupling of Dichlorobenzenes. Asian Journal of Organic Chemistry 2018, 7, 781–787. doi:10.1002/ajoc.201800001
  • Ibrahim, M. B.; Abdullahi, I. M.; Suleiman, R.; Fettouhi, M.; Ali, B. E. Merrifield’s Resin-Supported Palladium–Bis(oxazoline) Complex-Catalyzed Cross-Coupling Reactions of Aryl Bromides and Aryl Chlorides. Arabian Journal for Science and Engineering 2017, 43, 271–280. doi:10.1007/s13369-017-2946-8
  • Yang, J. Mono- and dinuclear N-heterocyclic carbene palladium complexes with diazine ligands and their catalytic activities toward the Mizoroki–Heck reaction. Journal of Coordination Chemistry 2017, 70, 3749–3758. doi:10.1080/00958972.2017.1395416
  • Bollu, R.; Banu, S.; Kasaboina, S.; Bantu, R.; Nagarapu, L.; Polepalli, S.; Jain, N. Potential anti-proliferative agents from 1,4-benzoxazinone-quinazolin-4(3H)-one templates. Bioorganic & medicinal chemistry letters 2017, 27, 5481–5484. doi:10.1016/j.bmcl.2017.10.044
  • Qingxian, L.; He, B.-Y.; Qian, P.-C.; Shao, L.-X. N-Heterocyclic carbene–palladium(II)–1-methylimidazole complex catalyzed direct C–H bond arylation of imidazo[1,2-a]pyridines with aryl chlorides. Organic & biomolecular chemistry 2017, 15, 1151–1154. doi:10.1039/c6ob02704k
  • Yin, S.-C.; Zhou, Q.; He, Q.-W.; Li, S.-W.; Qian, P.-C.; Shao, L.-X. N-Heterocyclic carbene-Pd(II)-1-methylimidazole complex catalyzed CH bond arylation of (benzo)thiophenes with aryl chlorides. Tetrahedron 2017, 73, 427–431. doi:10.1016/j.tet.2016.11.053
  • Yang, J. Synthesis and characterization of N-heterocyclic carbene–PdCl2–1H-benzotriazole complexes and their catalytic activities toward Mizoroki–Heck and Sonogashira reactions. Journal of Coordination Chemistry 2017, 70, 441–450. doi:10.1080/00958972.2016.1272676
  • Yin, S.-C.; Zhou, Y.-F.; Li, Y.; Qian, P.-C. The crystal structure of 1,3-bis(2,6-diiso-propylphenyl)imidazol-2-ylidene)-dibromido-(1-methyl-1H-imidazole-κ1N)palladium(II) – ethyl acetate – water (1/1/1), C31H42Br2N4Pd. Zeitschrift für Kristallographie - New Crystal Structures 2016, 232, 15–18. doi:10.1515/ncrs-2016-0107
  • Guo, M.; Fu, L.; Li, J.; Zhou, L.; Kang, Y. A Well-Defined {[(PhCH2O)2P(CH3)2CHNCH(CH3)2]2PdCl2} Complex Catalyzed Hiyama Coupling of Aryl Bromides with Arylsilanes. Molecules (Basel, Switzerland) 2016, 21, 987. doi:10.3390/molecules21080987
  • Ngnie, G.; Dedzo, G. K.; Detellier, C. Synthesis and catalytic application of palladium nanoparticles supported on kaolinite-based nanohybrid materials. Dalton transactions (Cambridge, England : 2003) 2016, 45, 9065–9072. doi:10.1039/c6dt00982d
  • Ji, Y.-Y.; Zhang, Y.; Hu, Y.-Y.; Shao, L.-X. N-heterocyclic carbene-Pd(II)-1-methylimidazole complex catalyzed C–H bond benzylation of (benzo)oxazoles with benzyl chlorides. Tetrahedron 2015, 71, 6818–6823. doi:10.1016/j.tet.2015.07.030
  • Gu, Z.-S.; Chen, W.-X.; Shao, L.-X. N-heterocyclic carbene-palladium(II)-1-methylimidazole complex-catalyzed direct C-H bond arylation of (benz)imidazoles with aryl chlorides. The Journal of organic chemistry 2015, 80, 8916–8921. doi:10.1021/acs.joc.5b01544
  • Yin, H.-Y.; Lin, X.-L.; Li, S.-W.; Shao, L.-X. N-heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed α-arylation reactions of tetralones with aryl chlorides and further transformation of the products. Organic & biomolecular chemistry 2015, 13, 9012–9021. doi:10.1039/c5ob01203a
  • Guest, D.; da Silva, V. H. M.; de Lima Batista, A. P.; Roe, S. M.; Braga, A. A. C.; Navarro, O. (N-Heterocyclic Carbene)-Palladate Complexes in Anionic Mizoroki-Heck Coupling Cycles: A Combined Experimental and Computational Study. Organometallics 2015, 34, 2463–2470. doi:10.1021/om5012038
Other Beilstein-Institut Open Science Activities