Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 23
193
Views
2
CrossRef citations to date
0
Altmetric
Articles

Synthesis of palladium nanoparticles using triazolium based ionic liquids: A reusable catalyst for addition of arylboronic acids to nitrostyrenes

, &
Pages 3000-3014 | Received 23 Apr 2018, Accepted 05 Oct 2018, Published online: 15 Nov 2018

References

  • Arya, S. K.; Saha, S.; Ramirez-Vick, J. E.; Gupta, V.; Bhansali, S.; Singh, S. P. Recent Advances in ZnO Nanostructures and Thin films for Biosensor Applications: Review. Analytica. Chimica. Acta. 2012, 737, 1–21. DOI: 10.1016/j.aca.2012.05.048.
  • Ma, Z.; Yu, J.; Dai, S. Preparation of Inorganic Materials Using Ionic Liquids. Adv. Mater. 2010, 22, 261–285. DOI: 10.1002/adma.200900603.
  • Torimoto, T.; Tsuda, T.; Okazaki, K.; Kuwabata, S. New Frontiers in Materials Science Opened by Ionic Liquids. Adv. Mater. 2010, 22, 1196–1221. DOI: 10.1002/adma.200902184.
  • Plechkova, N. V.; Seddon, K. R. Applications of Ionic Liquids in the Chemical Industry. Chem. Soc. Rev. 2008, 37, 123–150. DOI: 10.1039/b006677j.
  • Parvulescu, V. I.; Hardacre, C. Catalysis in Ionic Liquids. Chem. Rev. 2007, 107, 2615–2665. DOI: 10.1021/cr050948h.
  • Vestergaard, B.; Bjerrum, N. J.; Petrushina, I.; Hjuler, H. A.; Berg, R. W.; Begtrup, M. Molten Triazolium Chloride Systems as New Aluminum Battery Electrolytes. J. Electrochem. Soc. 1993, 140, 3108–3113. DOI: 10.1149/1.2220994.
  • Astleford, B. A.; Goe, G. L.; Keay, J. G.; Scriven, E. F. V. Synthesis of l-Alkyl-1,2,4-Triazoles: A New One-Pot Regiospecific Procedure. J. Org. Chem. 1989, 54, 731–732. DOI: 10.1021/jo00264a048.
  • Garratt, P. J. Comprehensive Heterocyclic Chemistry II; Elsevier, 1996.
  • Katritzky, A.; Pozharskii.; Ramsden, C. A.; Joule, J.; Zhdankin, V. Handbook of Heterocyclic Chemistry, 2nd ed.; Academic Press, Cambridge, Massachusetts, 2000.
  • Dalvie, D. K.; Kalgutkar, A. S.; Khojasteh-Bakht, S. C.; Obach, R. S.; O'Donnell, J. P. Biotransformation Reactions of Five-Membered Aromatic Heterocyclic Rings. Chem. Res. Toxicol. 2002, 15, 269–299. DOI: 10.1021/tx015574b.
  • Olofson, R. A.; Kendall, R. V. Protection by Acylation in the Selective Alkylation of Heterocycles. J. Org. Chem. 1970, 35, 2246–2248. DOI: 10.1021/jo00832a031.
  • Dupont, J.; Scholten, J. D. On the Structural and Surface Properties of Transition-Metal Nanoparticles in Ionic Liquids. Chem. Soc. Rev. 2010, 39, 1780–1804. DOI: 10.1039/b822551f.
  • Wang, R.; Jin, C. M.; Twamley, B.; Shreeve, J. M. Syntheses and Characterization of Unsymmetric Dicationic Salts Incorporating Imidazolium and Triazolium Functionalities. Inorg. Chem. 2006, 45, 6396–6403. DOI: 10.1021/ic060822i.
  • Dupont, J. On the Solid, Liquid and Solution Structural Organization of Imidazolium Ionic Liquids. J. Braz. Chem. Soc. 2004, 15, 341–350. DOI: 10.1590/s0103-50532004000300002.
  • Crosthwaite, J. M.; Aki, S. K. V. K.; Maginn, E. J.; Brennecke, J. F. Liquid Phase Behavior of Imidazolium-Based Ionic Liquids with Alcohols. J. Phys. Chem. B. 2004, 108, 5113–5119. DOI: 10.1021/jp037774x.
  • Mirzaei, Y. R.; Twamley, B.; Shreeve, J. M. Syntheses of 1-Alkyl-1,2,4-Triazoles and the Formation of Quaternary 1-Alkyl-4-Polyfluoroalkyl-1,2,4-Triazolium Salts Leading to Ionic Liquids. J. Org. Chem. 2002, 67, 9340–9345. DOI: 10.1021/jo026350g.
  • Seddon, K. R.; Stark, A.; Torres, M.-J. Influence of Chloride, Water, and Organic Solvents on the Physical Properties of Ionic Liquids. Pure Appl. Chem. 2000, 72, 2275–2287.DOI: 10.1351/pac200072122275.
  • Daily, L. A.; Miller, K. M. Correlating Structure with Thermal Properties for a Series of 1-Alkyl4-Methyl-1,2,4-Triazolium Ionic Liquids. J. Org. Chem. 2013, 78, 4196–4201. DOI: 10.1021/jo4003932.
  • Luo, J.; Hu, J.; Saak, W.; Beckhaus, R.; Wittstock, G.; Vankelecom, I. F. J.; Agert, C.; Conrad, O. Protic Ionic Liquid and Ionic Melts Prepared from Methanesulfonic Acid and 1H-1,2,4-Triazole as High Temperature PEMFC Electrolytes. J. Mater. Chem. 2011, 21, 10426–10436. DOI: 10.1039/c0jm04306k.
  • Gnanamgari, D.; Moores, A.; Rajaseelan, E.; Crabtree, R. H. Transfer Hydrogenation of Imines and Alkenes and Direct Reductive Amination of Aldehydes Catalyzed by Triazole-Derived Iridium(I) Carbene Complexes. Organometallics. 2007, 26, 1226–1230. DOI: 10.1021/om060938m.
  • Xue, H.; Twamley, B.; Shreeve, J. M. The First 1-Alkyl-3-Perfluoroalkyl-4,5-Dimethyl-1,2,4-Triazolium Salts. J. Org. Chem. 2004, 69, 1397–1400. DOI: 10.1021/jo0356107.
  • Dzyuba, S. V.; Kollar, K. D.; Sabnis, S. S. Synthesis of Imidazolium Room-Temperature Ionic Liquids. J. Chem. Educ. 2009, 86, 856–858. DOI: 10.1021/ed086p856.
  • Williamson, C. L.; Maly, K. E.; MacNeil, S. L. Synthesis of Imidazolium Room-Temperature Ionic Liquids: A Follow-Up to the Procedure of Dzyuba, Kollar, and Sabnis. J. Chem. Educ. 2013, 90, 799–801. DOI: 10.1021/ed300369m.
  • Nagarajan, S.; Kandasamy, E. Reusable 1,2,4-Triazolium Based Brønsted Acidic Room Temperature Ionic Liquids as Catalyst for Mannich Base Reaction. Catal. Catal. Lett. 2014, 144, 1507–1514. DOI: 10.1007/s10562-014-1312-7.
  • Wilkes, J. S. Properties of Ionic Liquid Solvents for Catalysis. J. Mol. Catal A: Chem. 2004, 214, 11–17. DOI: 10.1016/j.molcata.2003.11.029.
  • Welton, T. Ionic Liquids in Catalysis. Coord. Chem. Rev. 2004, 248, 2459–2477. DOI: 10.1016/j.ccr.2004.04.015.
  • Gu, Y.; Shi, F.; Deng, Y. Ionic Liquid as an Efficient Promoting Medium for Fixation of CO2: Clean Synthesis of α-Methylene Cyclic Carbonates from CO2 and Propargyl Alcohols Catalyzed by Metal Salts under Mild Conditions. J. Org. Chem. 2004, 69, 391–394. DOI: 10.1021/jo0351365.
  • Dupont, J.; Spencer, J. On the Noninnocent Nature of 1,3-Dialkylimidazolium Ionic Liquids. Angew. Chem. Int. Ed. 2004, 43, 5296–5297. DOI: 10.1002/anie.200460431.
  • Calo, V.; Nacci, A.; Monopoli, A.; Montingelli, F. Pd Nanoparticles as Efficient Catalysts for Suzuki and Stille Coupling Reactions of Aryl Halides in Ionic Liquids. J. Org. Chem. 2005, 70, 6040–6044. DOI: 10.1021/jo050801q.
  • Fihri, A.; Bouhrara, M.; Nekoueishahraki, B.; Basset, J. M.; Polshettiwar, V. Nanocatalysts for Suzuki Cross-Coupling Reactions. Chem. Soc. Rev. 2011, 40, 5181–5203. DOI: 10.1039/clcs15079k.
  • Mu, X. D.; Evans, D. G.; Kou, Y. A General Method for Preparation of PVP-Stabilized Noble Metal Nanoparticles in Room Temperature Ionic Liquids. Catal. Lett. 2004, 97, 151–154., DOI: 10.1023/b:catl.0000038577.18441.bf.
  • Calo, V.; Nacci, A.; Monopoli, A.; Laera, S.; Cioffi, N. Pd Nanoparticles Catalyzed Stereospecific Synthesis of β-Aryl Cinnamic Esters in Ionic Liquids. J. Org. Chem. 2003, 68, 2929–2933. DOI: 10.1021/jo026877t.
  • Prechtl, M. H. G.; Scholten, J. D.; Dupont, J. Carbon-Carbon Cross Coupling Reactions in Ionic Liquids Catalysed by Palladium Metal Nanoparticles. Molecules. 2010, 15, 3441–3461. DOI: 10.3390/molecules15053441.
  • Venkatesan, R.; Prechtl, M. H. G.; Scholten, J. D.; Pezzi, R. P.; Machado, G.; Dupont, J. Palladium Nanoparticle Catalysts in Ionic Liquids: synthesis, Characterization and Selective Partial Hydrogenation of Alkynes to Z-Alkenes. J. Mater. Chem. 2011, 21, 3030–3036. DOI: 10.1039/c0jm03557b.
  • Calo, V.; Nacci, A.; Monopoli, A.; Fornaro, A.; Sabbatini, L.; Cioffi, N.; Ditaranto, N. Heck Reaction Catalyzed by Nanosized Palladium on Chitosan in Ionic Liquids. Organometallics. 2004, 23, 5154–5158. DOI: 10.1021/om049586e.
  • Safavi, A.; Maleki, N.; Iranpoor, N.; Firouzabadi, H.; Banazadeh, A. R.; Azadi, R.; Sedaghati, F.; Highly, efficient, Stable, Palladium Nanocatalysts Supported on an Ionic Liquid-Modified Xerogel. Chem. Commun. 2008, 6155–6157. DOI: 10.1039/b814559h.
  • Yang, X.; Fei, Z.; Zhao, D.; Ang, W. H.; Li, Y.; Dyson, P. J. Palladium Nanoparticles Stabilized by an Ionic Polymer and Ionic Liquid: A Versatile System for C-C Cross-Coupling Reactions. Inorg. Chem. 2008, 47, 3292–3297. DOI: 10.1021/ic702305t.
  • Cassol, C. C.; Umpierre, A. P.; Machado, G.; Wolke, S. I.; Dupont, J. The Role of Pd Nanoparticles in Ionic Liquid in the Heck Reaction. J. Am. Chem. Soc. 2005, 127, 3298–3299. DOI: 10.1021/ja0430043.
  • Faria, V. W.; Oliveira, D. G. M.; Kurz, M. H. S.; Goncalves, F. F.; Scheeren, C. W.; Rosa, G. R. Palladium Nanoparticles Supported in a Polymeric Membrane: an Efficient Phosphine-Free “Green” Catalyst for Suzuki–Miyaura Reactions in Water. RSC Adv. 2014, 4, 13446–13452. DOI: 10.1039/c4ra01104.
  • Zhao, D.; Fei, Z.; Geldbach, T. J.; Scopelliti, R.; Dyson, P. J. Nitrile-Functionalized Pyridinium Ionic Liquids: Synthesis, Characterization, and Their Application in Carbon-Carbon Coupling Reactions. J. Am. Chem. Soc. 2004, 126, 15876–15882. DOI: 10.1021/ja0463482.
  • Lee, J. K.; Kim, M. J. Hydrogenation of Aryl Ketones Using Palladium Nanoparticles on Single-Walled Carbon Nanotubes in an Ionic Liquid. Tetrahedron Lett. 2011, 52, 499–501. DOI: 10.1016/j.tetlet.2010.11.081.
  • Calo, V.; Nacci, A.; Monopoli, A.; Cotugno, P. Heck Reactions with Palladium Nanoparticles in Ionic Liquids: Coupling of Aryl Chlorides with Deactivated Olefins. Angew. Chem. Int. Ed. 2009, 48, 6101–6103. DOI: 10.1002/anie.200902337.
  • Umpierre, A. P.; Machado, G.; Fecher, G. H.; Morais, J.; Dupont, J. Selective Hydrogenation of 1,3-Butadiene to 1-Butene by Pd(0) Nanoparticles Embedded in Imidazolium Ionic Liquids. Adv. Synth. Catal. 2005, 347, 1404–1412. DOI: 10.1002/adsc.200404313.
  • Huang, J.; Jiang, T.; Han, B.; Gao, H.; Chang, Y.; Zhao, G.; Wu, W. Hydrogenation of Olefins Using Ligand-Stabilized Palladium Nanoparticles in an Ionic Liquid. Chem. Commun. 2003, 1654–1655. DOI: 10.1039/b302750c.
  • Huang, J.; Jiang, T.; Gao, H.; Han, B.; Liu, Z.; Wu, W.; Chang, Y.; Zhao, G. Pd Nanoparticles Immobilized on Molecular Sieves by Ionic Liquids: Heterogeneous Catalysts for Solvent-Free Hydrogenation. Angew. Chem. Int. Ed. 2004, 43, 1397–1399. DOI: 10.1002/anie.200352682.
  • Hu, Y.; Yu, Y.; Hou, Z.; Li, H.; Zhao, X.; Feng, B. Biphasic Hydrogenation of Olefins by Functionalized Ionic Liquid-Stabilized Palladium Nanoparticles. Adv. Synth. Catal. 2008, 350, 2077–2085. DOI: 10.1002/adsc.200800290.
  • He, Q.; Xie, F.; Fu, G.; Quan, M.; Shen, C.; Yang, G.; Gridnev, I. D.; Zhang, W. Palladium-Catalyzed Asymmetric Addition of Arylboronic Acids to Nitrostyrenes. Org. Lett. 2015, 17, 2250–2253. DOI: 10.1021/acs.orglett.5b00863.
  • Wang, Z.-Q.; Feng, C.-G.; Zhang, S.-S.; Xu, M.-H.; Lin, G.-Q. Rhodium-Catalyzed Asymmetric Conjugate Addition of Organoboronic Acids to Nitroalkenes Using Chiral Bicyclo[3.3.0] Diene Ligands. Angew. Chem. Int. Ed. 2010, 49, 5780–5783. DOI: 10.1002/anie.201001883.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.