124
Views
0
CrossRef citations to date
0
Altmetric
Review Articles

Synthetic methodologies and applications of chalcogen (S, Se, Te) ionic liquids: a review

ORCID Icon
Pages 103-111 | Received 05 Jun 2023, Accepted 09 Sep 2023, Published online: 28 Sep 2023

References

  • Anastas, P. T.; Williamson, T. C. Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes; Oxford University Press: Oxford, 1998.
  • Adams, D. J.; Dyson, P. J.; Tavener, S. J. Chemistry in Alternative Reaction Media; John Wiley & Sons: Chichester, UK, 2004.
  • Welton, T. Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. Chem. Rev. 1999, 99, 2071–2084. DOI: 10.1021/cr980032t.
  • Wassercheid, P.; Welton, T. Ionic Liquids in Synthesis, 2nd ed.; Wiley-VCH: New York, NY, 2008.
  • Butcher, T. S.; Detty, M. R. Debrominations of vic-Dibromides with Diorganotellurides, Rate Constants, Erying and Arrhenius Activation Parameters and Mechanistic Implications. J. Org. Chem. 1999, 64, 5677–5681. DOI: 10.1021/jo990332q.
  • Petragnani, N.; Comasseto, J. V. Tellurium Reagents in Organic Synthesis; Recent Advances. Synthesis 1991, 1991, 793–817. DOI: 10.1055/s-1991-26577.
  • Engman, L. Synthetic Applications of Organotellurium Chemistry. Acc. Chem. Res. 1985, 18, 274–279. DOI: 10.1021/ar00117a003.
  • Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis. Organic Chemistry Series 4; Baldwin, J. E., Ed.; Pergamon: Oxford, 1986.
  • Topics in Current Chemistry, Organoselenium Chemistry: Modern Developments in Organic Synthesis; Wirth, T., Ed.; Springer: Germany, 2000.
  • Back, T. G.; King, R. B. Selenium: Organoselenium Chemistry in Encyclopedia of Inorganic Chemistry; John Wiley and Sons: Chichester, England, 1994.
  • Metzner, P.; Thuillier, A. Sulfur Reagents in Organic Synthesis; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Academic: San Diego, CA, 1994.
  • Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, NY, 1991; p 6.
  • Petragnani, N. Tellurium in Organic Synthesis; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Academic: San Diego, CA, 1994.
  • Comasseto, J. V.; Barientos-Astigarraga, R. E. Add a Little Tellurium to Your Synthetic Plans. Aldrichimica Acta 2000, 33, 66–78.
  • Mugesh, G.; Panda, A.; Singh, H. B.; Punekar, N. S.; Butcher, R. J. Glutathione Peroxidase-like Antioxidant Activity of Diaryl Diselenides: A Mechanistic Study. J. Am. Chem. Soc. 2001, 123, 839–850. DOI: 10.1021/ja994467p.
  • Mugesh, G.; Du Mont, W.-W.; Sies, H. Chemistry of Biologically Important Synthetic Organoselenium Compounds. Chem. Rev. 2001, 101, 2125–2179. DOI: 10.1021/cr000426w.
  • Wudl, F.; Schafer, D. E.; Miller, B. Dehydrotetrathianaphthazarin. J. Am. Chem. Soc. 1976, 98, 252–254. DOI: 10.1021/ja00417a050.
  • Irgolic, K. J. Tellurium: Literature Survey Covering the Year 1979. J. Organomet. Chem. 1980, 203, 367–414. DOI: 10.1016/S0022-328X(00)83957-1.
  • Olah, G. A.; Nojima, M.; Kerekes, I. Synthetic Methods and Reactions Selenium Tetrafluoride and Its Pyridine Complex. Convenient Fluorinating Agents for Fluorination of Ketones, Aldehydes, Amides, Alcohols, Carboxylic Acids and Anhydrides. J. Am. Chem. Soc. 1974, 96, 925–927. DOI: 10.1021/ja00810a052.
  • Bochmann, M. Metal Chalcogenide Materials: Chalcogenolato Complexes as “Single Source” Precursors. Chem. Vap. Deposition 1996, 2, 85–96. DOI: 10.1002/cvde.19960020302.
  • Wudl, F. From Organic Metals to Superconductors Managing Conduction Electrons in Organic Solids. Acc. Chem. Res. 1984, 17, 227–232. DOI: 10.1021/ar00102a005.
  • Wang, Y.; Zhang, W.; Colandrea, V. J.; Jimenez, L. S. Reactivity and Rearrangements of Dialkyl- and Diarylvinylsulfonium Salts with Indole-2- and Pyrrole-2-Carboxaldehydes. Tetrahedron 1999, 55, 10659–10672. DOI: 10.1016/S0040-4020(99)00605-5.
  • Xu, Y.; Fletcher, M.; Dolbier, W. R. Jr. Synthesis and Novel Reactivity of Halomethyldimethylsulfonium Salts. J. Org. Chem. 2000, 65, 3460–3465. DOI: 10.1021/jo000015f.
  • Aggarwal, V. K.; Fang, G. Y.; Schmidt, A. T. Synthesis and Applications of Chiral Organoboranes Generated from Sulfonium Ylides. J. Am. Chem. Soc. 2005, 127, 1642–1643. DOI: 10.1021/ja043632k.
  • Zhao, D.; Fei, Z.; Ang, W.; Dyson, P. Sulfonium-Based Ionic Liquids Incorporating the Allyl Functionality. IJMS 2007, 8, 304–315. DOI: 10.3390/i8040304.
  • Hoffman, J. L. Ion Chromatographic Analysis of the Purity and Synthesis of Sulfonium and Selenonium Ions. J. Chromatogr. 1991, 588, 211–216. DOI: 10.1016/0021-9673(91)85025-B.
  • Gong, Y.; Li, Y.; Hu, J.; Wang, Z.; Deng, T. Sulfur-Containing Amino Acid-Derived Ionic Liquid as a Halogen-Free Catalyst for CO2 Mild Transformation into Cyclic Carbonates. New J. Chem. 2021, 45, 19215–19218. DOI: 10.1039/D1NJ03332H.
  • Zhao, H. Protein Stabilization and Enzyme Activation in Ionic Liquids: Specific Ion Effects. J. Chem. Technol. Biotechnol. 2016, 91, 25–50. DOI: 10.1002/jctb.4837.
  • Itoh, T.; Ouchi, N.; Hayase, S.; Nishimura, Y. Lipase-Catalyzed Enantioselective Acylation in a Halogen Free Ionic Liquid Solvent System. Chem. Lett. 2003, 32, 654–655. DOI: 10.1246/cl.2003.654.
  • Tsukada, Y.; Iwamoto, K.; Furutani, H.; Matsushita, Y.; Abe, Y.; Matsumoto, K.; Monda, K.; Hayase, S.; Kawatsura, M.; Itoh, T. Preparation of Novel Hydrophobic Fluorine-Substituted-Alkyl Sulfate Ionic Liquids and Application as an Efficient Reaction Medium for Lipase-Catalyzed Reaction. Tetrahedron Lett. 2006, 47, 1801–1804. DOI: 10.1016/j.tetlet.2006.01.017.
  • Itoh, T.; Han, S.; Matsushita, Y.; Hayase, S. Enhanced Enantioselectivity and Remarkable Acceleration on the Lipase-Catalyzed Transesterification Using Novel Ionic Liquids. Green Chem. 2004, 6, 437–439. DOI: 10.1039/b405396f.
  • Itoh, T.; Matsushita, Y.; Abe, Y.; Han, S.-H.; Wada, S.; Hayase, S.; Kawatsura, M.; Takai, S.; Morimoto, M.; Hirose, Y. Enhanced Enantioselectivity and Remarkable Acceleration of Lipase-Catalyzed Transesterification Using an Imizadolium PEG-Alkyl Sulfate Ionic Liquid. Chemistry 2006, 12, 9228–9237. DOI: 10.1002/chem.200601043.
  • Kadotani, S.; Inagaki, R.; Nishihara, T.; Nokami, T.; Itoh, T. Enhanced Activity of a Lipase by the Coating with Tris(Diethylamino)Cyclopropenium Alkyl-PEG Sulfate Ionic Liquid and Cooperative Activation with an Amino Acid. ACS Sustainable Chem. Eng. 2017, 5, 8541–8545. DOI: 10.1021/acssuschemeng.7b02607.
  • Nishihara, T.; Shiomi, A.; Kadotani, S.; Nokami, T.; Itoh, T. Remarkable Improved Stability and Enhanced Activity of a Burkholderia cepacia Lipase by the Coating with a Triazolium Alkyl-PEG Sulfate Ionic Liquid. Green Chem. 2017, 19, 5250–5256. DOI: 10.1039/C7GC02319G.
  • Itoh, T. Ionic Liquids as Tool to Improve Enzymatic Organic Synthesis. Chem. Rev. 2017, 117, 10567–10607. DOI: 10.1021/acs.chemrev.7b00158.
  • Klayman, D. L.; Gunter, H. H. Organoselenium Compounds: Their Chemistry and Biology; Wiley-Interscience: New York, 1973.
  • Shamberger, R. J. Biochemistry of Selenium; Plenum Press: New York, 1983. DOI: 10.1007/978-1-4684-4313-4_8.
  • Zhan, P.; Liu, X.; Fang, Z.; Pannecouque, C.; Clercq, E. D. 1,2,3-Selenadiazole Thioacetanilides: Synthesis and anti-HIV Activity Evaluation. Bioorg. Med. Chem. 2009, 17, 6374–6379. DOI: 10.1016/j.bmc.2009.07.027.
  • Alexander, V.; Choi, W. J.; Chun, J.; Kim, H. O.; Jeon, J. H.; Tosh, D. K.; Lee, H. W.; Chandra, G.; Choi, J.; Jeong, L. S. A New DNA Building Block, 4’-Selenothymidine: Synthesis and Modification to 4’-Seleno-AZT as a Potential anti-HIV Agent. Org. Lett. 2010, 12, 2242–2245. DOI: 10.1021/ol1005906.
  • Chou, L.-C.; Huang, L.-J.; Hsu, M.-H.; Fang, M.-C.; Yang, J.-S.; Zhuang, S.-H.; Lin, H.-Y.; Lee, F.-Y.; Teng, C.-M.; Kuo, S.-C. Synthesis of 1-Benzyl-3-(5-Hydroxymethyl-2-Furyl)Selenolo[3,2-c]Pyrazole Derivatives as New Anticancer Agents. Eur. J. Med. Chem. 2010, 45, 1395–1402. DOI: 10.1016/j.ejmech.2009.12.039.
  • Braga, H. C.; Stefani, H. A.; Paixão, M. W.; Santos, F. W.; Ludtke, D. S. Synthesis of 5’-Seleno-Xylofuranosides. Tetrahedron 2010, 66, 3441–3446. DOI: 10.1016/j.tet.2010.03.033.
  • Alberto, E. E.; Soares, L. C.; Sudati, J. H.; Borges, A. C. A.; Rocha, J. B. T.; Braga, A. L. Efficient Synthesis of Modular Amino Acid Derivatives Containing Selenioum with Pronounced GPx-like Activity. Eur. J. Org. Chem. 2009, 2009, 4211–4214. DOI: 10.1002/ejoc.200900485.
  • Jacob, C.; Giles, G. I.; Giles, N. M.; Sies, H. Sulfur and Selenium: The Role of Oxidation State in Protein Structure and Function. Angew. Chem. Int. Ed. Engl. 2003, 42, 4742–4758. DOI: 10.1002/anie.200300573.
  • Nogueira, C. W.; Zeni, G.; Rocha, J. B. T. Organoselenium and Organotellurium Compounds: Toxicology and Pharmacology. Chem. Rev. 2004, 104, 6255–6285. DOI: 10.1021/cr0406559.
  • Hwu, J. R.; Lai, L. L.; Hakimelahi, G. H.; Davari, H. Synthesis of First Selenium Containing Bicyclic β–Lactams as Potent Antimicrobial Agents. Helv. Chim. Acta 1994, 77, 1037–1045. DOI: 10.1002/hlca.19940770416.
  • Hafez, S. H. A. Selenium Containing Hetrocycles, Synthesis and Reactions of 2-Amino-4,5,6,7-Tetrahydro-1-Benzoselenophene-3-Carbonitrile with Anticipated Biological Activity. Russ. J. Org. Chem. 2005, 41, 396–401. DOI: 10.1007/s11178-005-0177-z.
  • Victoria, F. N.; Radatz, C. S.; Sachini, M.; Jacob, R. G.; Perin, G.; Silva, W. P.; Lenardão, E. J. KF/Al2O3 and PEG-400 as Arecyclable Medium for the Selective α–Selenation of Aldehydes and Ketones. Preparation of Potential Antimicrobial Agent. Tetrahedron Lett. 2009, 50, 6761–6763. DOI: 10.1016/j.tetlet.2009.09.093.
  • Alberto, E. E.; Rossato, L. L.; Alves, S. H.; Alves, D.; Braga, A. L. Imidazolium Ionic Liquids Containing Selenium: Synthesis and Antimicrobial Activity. Org. Biomol. Chem. 2011, 9, 1001–1003. DOI: 10.1039/c0ob01010c.
  • Kim, S. H.; Kim, Y. J.; Lee, H.; Park, K. Y.; Lee, C.; Chin, C. S. Ionic Liquids Containing Anionic Selenium Species: Applications for the Oxidative Carbonylation of Aniline. Angew. Chem. Int. Ed. 2002, 41, 4300–4303. DOI: 10.1002/1521-3773(20021115)41:22 < 4300::AID-ANIE4300 > 3.0.CO;2-V.
  • Thurow, S.; Pereira, V. A.; Martinez, D. M.; Alves, D.; Perin, G.; Jacob, R. G.; Lenardão, E. J. Base Free Oxidation of Thiols to Disulfides Using Selenium Ionic Liquids. Tetrahedron Lett. 2011, 52, 640–643. DOI: 10.1016/j.tetlet.2010.11.158.
  • Thurow, S.; Ostosi, N. T.; Mendes, S. R.; Jacob, R. G.; Lenardão, E. J. Synthesis of Vinyl Sulfides under Base Free Conditions Using Selenium Ionic Liquids. Tetrahedron Lett. 2012, 53, 2651–2653. DOI: 10.1016/j.tetlet.2012.03.076.
  • Zimmermann, E. G.; Thurow, S.; Freitas, C. S.; Mendes, S. R.; Perin, G.; Alves, D.; Jacob, R. G.; Lenardão, E. J. A Selenium Based Ionic Liquid as a Recyclable Solvent for the Catalyst Free Synthesis of 3-Selenyl Indoles. [Bmim] [SeO2 (OCH3)]. Molecules 2013, 18, 4081–4090. DOI: 10.3390/molecules18044081.
  • Zhang, F.; Wang, H.; Huimin, Z.; Fang, D.; Zang, S.; Zhao, G. Synthesis of Selenium Ionic Liquids and Its Application in Ethyl Benzene Oxidation. Sci. Sin-Chim. 2016, 46, 1350–1355. DOI: 10.1360/N032016-00108.
  • Lenardão, E. J.; Feijó, J. O.; Thurow, S.; Perin, G.; Jacob, R. G.; Silveira, C. C. Selenonium Ionic Liquid as Efficient Catalyst for the Baylis–Hillman Reaction. Tetrahedron Lett. 2009, 50, 5215–5217. DOI: 10.1016/j.tetlet.2009.06.132.
  • Lenardão, E. J.; Mendes, S. R.; Ferreira, P. C.; Perin, G.; Silveira, C. C.; Jacob, R. G. Selenium- and Tellurium-Based Ionic Liquids and Their Use in the Synthesis of Octahydroacridines. Tetrahedron Lett. 2006, 47, 7439–7442. DOI: 10.1016/j.tetlet.2006.08.049.
  • Lenardão, E. J.; Borges, E. L.; Mendes, S. R.; Perin, G.; Jacob, R. G. Selenonium Ionic Liquid as an Efficient Catalyst for the Synthesis of Thioacetals under Solvent-Free Conditions. Tetrahedron Lett. 2008, 49, 1919–1921. DOI: 10.1016/j.tetlet.2008.01.096.
  • Cheng, X. Y.; Li, K. F.; Wang, Q. J.; Wang, C. Y.; Ying, T. K. Oxidation of Alcohols to Aldehydes and Ketones Using Selenium Ionic Liquids. Chin. Chem. Lett. 2012, 23, 801–804. DOI: 10.1016/j.cclet.2012.05.019.

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.