Suzuki–Miyaura cross-coupling reaction of 1-aryltriazenes with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene–palladium complex catalyst

Guangming Nan, Fang Ren and Meiming Luo
Beilstein J. Org. Chem. 2010, 6, No. 70. https://doi.org/10.3762/bjoc.6.70

Cite the Following Article

Suzuki–Miyaura cross-coupling reaction of 1-aryltriazenes with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene–palladium complex catalyst
Guangming Nan, Fang Ren and Meiming Luo
Beilstein J. Org. Chem. 2010, 6, No. 70. https://doi.org/10.3762/bjoc.6.70

How to Cite

Nan, G.; Ren, F.; Luo, M. Beilstein J. Org. Chem. 2010, 6, No. 70. doi:10.3762/bjoc.6.70

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

  • Liu, T.; Wu, H.; Zhang, Q.; Wang, C. Recent advances in the chemistry of aryltriazene. Organic & biomolecular chemistry 2023, 21, 2059–2068. doi:10.1039/d2ob02267b
  • Mikra, C.; Mitrakas, A.; Ghizzani, V.; Katsani, K. R.; Koffa, M.; Koukourakis, M.; Psomas, G.; Protti, S.; Fagnoni, M.; Fylaktakidou, K. C. Effect of Arylazo Sulfones on DNA: Binding, Cleavage, Photocleavage, Molecular Docking Studies and Interaction with A375 Melanoma and Non-Cancer Cells. International journal of molecular sciences 2023, 24, 1834. doi:10.3390/ijms24031834
  • Rossi, R.; Ciofalo, M. Palladium-Catalysed Intermolecular Direct C–H Bond Arylation of Heteroarenes with Reagents Alternative to Aryl Halides: Current State of the Art. Current Organic Chemistry 2022, 26, 215–274. doi:10.2174/1385272826666220201124008
  • Götz, S.; Zechel, S.; Hager, M. D.; Newkome, G. R.; Schubert, U. S. Versatile Applications of Metallopolymers. Progress in Polymer Science 2021, 119, 101428. doi:10.1016/j.progpolymsci.2021.101428
  • Kim, K. M.; Kim, K. M. Copper Catalyzed N-Arylation of Amines in Ionic Liquid Using 1-Aryltriazenes as Aryl Surrogates. ChemistrySelect 2021, 6, 2709–2715. doi:10.1002/slct.202100180
  • Sanhueza, I. A.; Klauck, F. J. R.; Senol, E.; Keaveney, S. T.; Sperger, T.; Schoenebeck, F. Base‐Free Cross‐Couplings of Aryl Diazonium Salts in Methanol: Pd(II)‐Alkoxy as Reactivity‐Controlling Intermediate. Angewandte Chemie (International ed. in English) 2021, 60, 7007–7012. doi:10.1002/anie.202014842
  • Sanhueza, I. A.; Klauck, F. J. R.; Senol, E.; Keaveney, S. T.; Sperger, T.; Schoenebeck, F. Base‐Free Cross‐Couplings of Aryl Diazonium Salts in Methanol: PdII–Alkoxy as Reactivity‐Controlling Intermediate. Angewandte Chemie 2021, 133, 7083–7088. doi:10.1002/ange.202014842
  • Zhang, Y.; Tang, C.; Liu, Y.; Liu, C. Research Progress of Aryltriazene as Aryl Precursor and Aryl-Azo Precursors in Organic Synthesis. Chinese Journal of Organic Chemistry 2021, 41, 2587. doi:10.6023/cjoc202102014
  • Sutar, S. M.; Savanur, H. M.; Patil, C.; Prabhala, P.; Aridoss, G.; Kalkhambkar, R. G. Palladium Catalyzed Electrophilic C2-Arylation of Azoles by Aryltriazenes in Ionic Liquid Promoted by Acidic Ionic Liquid. ChemistrySelect 2020, 5, 12324–12327. doi:10.1002/slct.202002854
  • Jaishri, C.; Ajay, K. G.; Prabhat, K. B. An Overview of Solid Supported Palladium and Nickel Catalysts for C-C Cross Coupling Reactions. Mini-Reviews in Organic Chemistry 2020, 17, 589–604. doi:10.2174/1570193x16666190617160339
  • Wang, F.; Wang, C.; Sun, G.; Zou, G. Highly efficient palladium-catalyzed cross-coupling of diarylborinic acids with arenediazoniums for practical diaryl synthesis. Tetrahedron Letters 2020, 61, 151491. doi:10.1016/j.tetlet.2019.151491
  • Yang, Q.; Babij, N. R.; Good, S. Potential Safety Hazards Associated with Pd-Catalyzed Cross-Coupling Reactions. Organic Process Research & Development 2019, 23, 2608–2626. doi:10.1021/acs.oprd.9b00377
  • Liu, C.; Wang, Z.; Wang, L.; Li, P.; Zhang, Y. Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes. Organic & biomolecular chemistry 2019, 17, 9209–9216. doi:10.1039/c9ob01883b
  • Sutar, S. M.; Savanur, H. M.; Malunavar, S. S.; Prabhala, P.; Kalkhambkar, R. G.; Laali, K. K. 1‐Aryltriazenes in the Suzuki, Heck, and Sonogashira Reactions in Imidazolium‐ILs, with [BMIM(SO3H][OTf] or Sc(OTf)3 as Promoter, and Pd(OAc)2 or NiCl2.glyme as Catalyst. European Journal of Organic Chemistry 2019, 2019, 6088–6093. doi:10.1002/ejoc.201901070
  • Felpin, F.-X.; Sengupta, S. Biaryl synthesis with arenediazonium salts: cross-coupling, CH-arylation and annulation reactions. Chemical Society reviews 2019, 48, 1150–1193. doi:10.1039/c8cs00453f
  • Mao, S.; Chen, Z.; Wang, L.; Khadka, D. B.; Xin, M.; Li, P.; Zhang, S.-Q. Synthesis of Aryl Trimethylstannane via BF3·OEt2-Mediated Cross-Coupling of Hexaalkyl Distannane Reagent with Aryl Triazene at Room Temperature. The Journal of organic chemistry 2018, 84, 463–471. doi:10.1021/acs.joc.8b02766
  • Dai, W.-C.; Wang, Z.-X. Transition-Metal-Free Reaction of Aryltrimethylammonium Iodides with Arylzinc Reagents. Chemistry, an Asian journal 2017, 12, 3005–3009. doi:10.1002/asia.201701342
  • Sabounchei, S. J.; Hashemi, A.; Hosseinzadeh, M.; Salehzadeh, S.; Maleki, F. [60]Fullerene-Based Pd(0) Complexes of Phosphorus Ylides as Efficient Nanocatalyst for Homo- and Heterogeneous Mizoroki–Heck Coupling Reactions. Catalysis Letters 2017, 147, 2319–2331. doi:10.1007/s10562-017-2147-9
  • Mehdipour, E.; Shafieyoon, P.; Salahvarzi, M.; Amani, V. Tetrakis [N-(2-pyridyl) sulfonamide] di palladium: synthesize, X-ray diffraction, antibacterial properties and as a novel binuclear Pd-complex for coupling reactions. Journal of the Iranian Chemical Society 2017, 14, 1575–1582. doi:10.1007/s13738-017-1098-9
  • Zhong, R.; Lindhorst, A. C.; Groche, F. J.; Kühn, F. E. Immobilization of N-Heterocyclic Carbene Compounds: A Synthetic Perspective. Chemical reviews 2017, 117, 1970–2058. doi:10.1021/acs.chemrev.6b00631
Other Beilstein-Institut Open Science Activities