Cellulose sulfate: An efficient heterogeneous catalyst for the ring-opening of epoxides with alcohols and anilines

References

• Smith, J. G. Synthetically Useful Reactions of Epoxides. Synthesis. 1984, 8, 629–656. DOI: 10.1055/s-1984-30921.
   Google Scholar
• Ager, D. J.; Prakash, I.; Schaad, D. R. 1,2-Amino Alcohols and Their Heterocyclic Derivatives as Chiral Auxiliaries in Asymmetric Synthesis. Chem. Rev. 1996, 96, 835–876. DOI: 10.1021/cr9500038.
   PubMed Web of Science ®Google Scholar
• Corey, E. J.; Cheng, X. M. The Logic of Chemical Synthesis. New York: John Wiley, 1989.
   Google Scholar
• Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Recent Advances in the Preparation and Synthetic Applications of Oxiranes. Tetrahedron. 1983, 39, 2323–2367. DOI: 10.1016/S0040-4020(01)91961-1.
   Web of Science ®Google Scholar
• Reeve, W.; Christoffel, I. The Reaction of Styrene Oxide with Methanol. J. Am. Chem. Soc. 1950, 72, 1480–1483. DOI: 10.1021/ja01160a014.
   Web of Science ®Google Scholar
• Capes, A. S.; Crossman, A. T.; Webster, L. A.; Ferguson, M. A. J.; Gilbert, I. H. Investigation of Copper(II) Tetrafluoroborate Catalyzed Epoxide Opening. Tetrahedron Lett. 2011, 52, 7091–7094. DOI: 10.1016/j.tetlet.2011.10.090.
   PubMed Web of Science ®Google Scholar
• Kim, B. H.; Piao, F.; Lee, E. J.; Kim, J. S.; Jun, Y. M.; Lee, B. M. InCl3-Catalyzed Regioselective Ring-Opening Reactions of Epoxides to β-Hydroxy Ethers. Bull. Korean Chem. Soc. 2004, 25, 881–888. DOI: 10.5012/bkcs.2004.25.6.881.
   Web of Science ®Google Scholar
• Iranpoor, N.; Salehi, P. Highly Efficient, Regio- and Stereoselective Alcoholysis of Epoxides Catalyzed with Iron(III) Chloride. Synthesis. 1994, 1994, 1152–1154. DOI: 10.1055/s-1994-25661.
   Google Scholar
• Dalpozzo, R.; Nardi, M.; Oliverio, M.; Paonessa, R.; Procopio, A. Erbium(III) Triflate is a Highly Efficient Catalyst for the Synthesis of β-Alkoxy Alcohols, 1,2-Diols and β-Hydroxy Sulfides by Ring-Opening of Epoxides. Synthesis. 2009, 2009, 3433–3438. DOI: 10.1055/s-0029-1216956.
   Web of Science ®Google Scholar
• Salehi, P.; Seddighi, B.; Irandoost, M.; Behbahani, F. K. Ferric Perchlorate: An Efficient Reagent for Regio- and Stereoselective Alcoholysis and Hydrolysis of Epoxides. Synth. Commun. 2000, 30, 2967–2973. DOI: 10.1080/00397910008087447.
   Web of Science ®Google Scholar
• Taghavi, S. A.; Moghadam, M.; Baltork, I. M.; Tangestaninejad, S.; Mirkhani, V.; Khosropour, A. R.; Ahmadi, V. Investigaton of the Catalytic Activity of an Electron-Deficient Vanadium(IV) Tetraphenylporphyrin: A New, Highly Efficient and Reusable Catalyst for Ring-Opening of Epoxides. Polyhedron. 2011, 30, 2244–2252. DOI: 10.1016/j.poly.2011.06.008.
   Web of Science ®Google Scholar
• Venkatasubbaiah, K.; Feng, Y.; Arrowood, T.; Nickias, P.; Jones, C. W. Soluble and Supported Molecular CoIII Catalysts for the Regioselective Ring-Opening of 1,2-Epoxyhexane with Methanol. Chem. Cat. Chem. 2013, 5, 201–209. DOI: 10.1002/cctc.201200494.
   Web of Science ®Google Scholar
• Iranpoor, N.; Baltork, I. M. 2,3-Dichloro-5,6-Dicyano-p-Benzoquinone, an Efficient, Mild, Neutral and Highly Regioselective Catalyst for Alcoholysis of Epoxides. Tetrahedron Lett. 1990, 31, 735–738. DOI: 10.1016/S0040-4039(00)94616-1.
   Web of Science ®Google Scholar
• Uyanik, C.; Hanson, J. R.; Hitchcock, P. B.; Lazar, M. A. Steric Effects in the Tetracyanoethylene Catalyzed Methanolysis of Some Cyclohexane Epoxides. Tetrahedron. 2005, 61, 4323–4327. DOI: 10.1016/j.tet.2005.01.030.
   Web of Science ®Google Scholar
• Weil, T.; Kotke, M.; Kleiner, C. M.; Schreiner, P. R. Cooperative Brønsted Acid-Type Organocatalysis: Alcoholysis of Styrene Oxides. Org. Lett. 2008, 10, 1513–1516. DOI: 10.1021/ol800149y.
   PubMed Web of Science ®Google Scholar
• Deshpande, N.; Parulkar, A.; Joshi, R.; Diep, B.; Kulkarni, A.; Brunelli, N. A. Epoxide Ring-Opening with Alcohols Using Heterogeneous Lewis Acid Catalysts: Regioselectivity and Mechanism. J. Catal. 2019, 370, 46–54. DOI: 10.1016/j.jcat.2018.11.038.
   Web of Science ®Google Scholar
• Gharib, M.; Esrafili, L.; Morsali, A.; Retailleau, P. Solvent-Assisted Ligand Exchange (SALE) for the Enhancement of Epoxide Ring-Opening Reaction Catalysis Based on Three Amide-Functionalized Metal-Organic Frameworks. Dalton Trans. 2019, 48, 8803–8814. DOI: 10.1039/C9DT00941H.
   PubMed Web of Science ®Google Scholar
• Bruno, S. M.; Gomes, A. C.; Oliveira, T. S. M.; Antunes, M. M.; Lopes, A. D.; Valente, A. A.; Goncalves, I. S.; Pillinger, M. Catalytic Alcoholysis of Epoxides Using Metal-Free Cucurbituril-Based Solids. Org. Biomol. Chem. 2016, 14, 3873–3877. DOI: 10.1039/C6OB00512H.
   PubMed Web of Science ®Google Scholar
• Nakhate, A. V.; Yadav, G. D. Graphene-Oxide-Supported SO3H-Functionalized Imidazolium-Based Ionic Liquid: Efficient and Recyclable Heterogeneous Catalyst for Alcoholysis and Aminolysis Reactions. ChemistrySelect. 2018, 3, 4547–4556. DOI: 10.1002/slct.201703064.
   Web of Science ®Google Scholar
• Dhakshinamoorthy, A.; Alvaro, M.; Concepcion, P.; Fornes, V.; Garcia, H. Graphene Oxide as an Acid Catalyst for the Room Temperature Ring Opening of Epoxides. Chem. Commun. 2012, 48, 5443–5445. DOI: 10.1039/C2CC31385E.
   PubMed Web of Science ®Google Scholar
• Chauhan, M. S.; Yadav, G. D.; Hussain, F.; Singh, S. N-Fluorobenzenaminium Tetrafluoroborate Generated in Situ by Aniline and Selectfluor as a Reusable Catalyst for the Ring-Opening of Epoxides with Amines Under Microwave Irradiation. Catal. Sci. Technol. 2014, 4, 3945–3952. DOI: 10.1039/C4CY00609G.
   Web of Science ®Google Scholar
• Dixit, A.; Yadav, G. D.; Chauhan, M. S.; Singh, S. Salts of 1-(Chloromethyl)-DABCO: A Highly Efficient Organocatalyst for the Alcoholysis of Epoxides. Ccat. 2016, 5, 203–211. DOI: 10.2174/2211544705666160802142555.
   Google Scholar
• Klemm, D.; Heublein, B.; Fink, H.-P.; Bohn, A. Cellulose: Fascinating Biopolymer and Sustainable Raw Material. Angew. Chem. Int. Ed. Engl. 2005, 44, 3358–3393. DOI: 10.1002/anie.200460587.
   PubMed Web of Science ®Google Scholar
• Shaabani, A.; Maleki, A.; Rad, J. M.; Soleimani, E. Cellulose Sulfuric Acid Catalyzed One-Pot Three-Component Synthesis of Imidazoazines. Chem. Pharm. Bull. 2007, 55, 957–958. DOI: 10.1248/cpb.55.957.
   PubMed Web of Science ®Google Scholar
• Dachavaram, S. S.; Penthala, N. R.; Calahan, J. L.; Munson, E. J.; Crooks, P. A. Highly Sulphated Cellulose: A Versatile, Reusable and Selective Desilylating Agent for Deprotection of Alcoholic TBDMS Ethers. Org. Biomol. Chem. 2018, 16, 6057–6062. DOI: 10.1039/C8OB01438H.
   PubMed Web of Science ®Google Scholar
• Vekariya, R. H.; Patel, H. D. Cellulose Sulfuric Acid (CSA) and Starch Sulfuric Acid (SSA) as Solid and Heterogeneous Catalysts in Green Organic Synthesis: Recent Advances. Arkivoc. 2015, 2015, 136–159. DOI: 10.3998/ark.5550190.p008.975.
   Web of Science ®Google Scholar
• Nikoofar, K.; Heidari, H.; Shahedi, Y. Nano Crystalline Cellulose Sulfuric Acid (s-NCC): A Novel Green Nanocatalyst for the Synthesis of Polyhydroxypyrimidine-Fused Heterocyclic Compounds (PPFHs). Cellulose. 2018, 25, 5697–5709. DOI: 10.1007/s10570-018-1942-9.
   Web of Science ®Google Scholar
• Whistler, R. L.; Spencer, W. W. Preparation and Properties of Several Polysacharide Sulfates. Arch. Biochem. Biophys. 1961, 95, 36–41. DOI: 10.1016/0003-9861(61)90105-9.
   PubMed Web of Science ®Google Scholar
• Chen, G.; Zhang, B.; Zhao, J.; Chen, H. Improved Process for the Production of Cellulose Sulfate Using Sulfuric Acid/Ethanol Solution. Carbohydr. Polym. 2013, 95, 332–337. DOI: 10.1016/j.carbpol.2013.03.003.
   PubMed Web of Science ®Google Scholar
• Bhatt, N.; Gupta, P. K.; Naithani, S. Preparation of Cellulose Sulfate from α-Cellulose Isolated from Lantana Camara by the Direct Esterification Method. J. Appl. Polym. Sci. 2008, 108, 2895–2901. DOI: 10.1002/app.27773.
   Web of Science ®Google Scholar
• Kowsaka, K.; Okajima, K.; Kamide, K. Determination of the Distribution of Substituent Groups in Sodium Cellulose Sulfate: Assignment of 1H and 13C NMR Peaks by Two-Dimensional COSY and CH-COSY Methods. Polym. J. 1991, 23, 823–836. DOI: 10.1295/polymj.23.823.
   Web of Science ®Google Scholar