An Efficient and Convenient Approach for Synthesizing Iodohydrin and Iodoether from Aromatic Alkenes Using Hg(BF₄)₂.SiO₂ and I₂

References

• C. Christophersen, “Secondary Metabolites from Marine  Bryozoans. A Review,”Acta Chemica Scandinavica Series B 39, no. 7 (1985): 517–29.
   PubMedGoogle Scholar
• P. Swamy, M. A. Kumar, M. M. Reddy, M. Naresh, K. Srujana, and N. Narender, “The Vicinal Functionalization of Olefins: A Facile Route to the Direct Synthesis of β-Chlorohydrins and β-Chloroethers,”RSC Advances 4, no. 50 (2014): 26288–94.
   Web of Science ®Google Scholar
• A. Tenaglia, O. Pardigon, and G. Buono, “Regio-and Stereoselective Functionalization of Deltacyclenes: A Route to the Synthesis of Optically Active (+)-Deltacyclan-8-One,” The Journal of Organic Chemistry 61, no. 3 (1996): 1129–32.
   Web of Science ®Google Scholar
• D. Dolenc, and M. Harej, “Direct Conversion of Bromohydrins to Ketones by a Free Radical Elimination of Hydrogen Bromide1,”The Journal of organic chemistry 67, no. 1 (2002): 312–3.
   PubMed Web of Science ®Google Scholar
• N. Iranpoor, and M. Shekarriz, “Regioselective 1,2-Alkoxy, Hydroxy, and Acetoxy Iodination of Alkenes with I2 Catalyzed by Ce(SO3CF3)4,”Tetrahedron 56, no. 29 (2000): 5209–11.
   Web of Science ®Google Scholar
• B. Yang, and Z. Lu, “Visible-Light-Promoted Metal-Free Aerobic Hydroxyazidation of Alkenes,”ACS Catalysis 7, no. 12 (2017): 8362–5.
   Web of Science ®Google Scholar
• I. Cabanal-Duvillard, J.-F. Berrien, J. Royer, and H.-P. Husson, “Expeditious Formal Synthesis of (±)-Epibatidine Using Diastereoselective Bromohydroxylation of Aminocyclohexene Derivatives,”Tetrahedron Letters 39, no. 29 (1998): 5181–4.
   Web of Science ®Google Scholar
• F. Tian, G. Yan, and J. Yu, “Recent Advances in the Synthesis and Applications of α-(trifluoromethyl)styrenes in organic synthesis,”Chemical Communications (Cambridge, England) 55, no. 90 (2019): 13486–505.
   PubMed Web of Science ®Google Scholar
• R. C. Cambie, W. I. Noall, G. J. Potter, P. S. Rutledge, and P. D. Woodgate, “Reactions of Alkenes with Electrophilic Iodine in Tetramethylene Sulphone–Chloroform,” Journal of the Chemical Society, Perkin Transactions 1, no. 3 (1977): 226–30.
   Google Scholar
• L. Bering, and A. P. Antonchick, “Selective Transition-Metal-Free Vicinal Cis-Dihydroxylation of Saturated Hydrocarbons,” Chemical Science 8, no. 1 (2017): 452–7.
   PubMed Web of Science ®Google Scholar
• J. W. Cornforth, and D. T. Green, “Iodohydrins and Epoxides from Olefins,” Journal of the Chemical Society C: Organic no. 6 (1970) : 846–9.
   Web of Science ®Google Scholar
• J. Barluenga, J. M. González, P. J. Campos, and G. Asensio, “I(Py)2BF4, a New Reagent in Organic Synthesis: General Method for the 1,2‐Iodofunctionalization of Olefins,” Angewandte Chemie International Edition in English 24, no. 4 (1985): 319–20.
   Web of Science ®Google Scholar
• M. C. S. de Mattos, and A. M. Sanseverino,“Fe2(SO4)3-Mediated Coiodination of Alkenes with Acetic Acid: A Convenient and Regioselective Eco-Friendly Preparation of β-Iodoacetates,” Journal of Chemical Research 2004, no. 9 (2004): 638–9.
   Google Scholar
• J. Barluenga, M. A. Rodríguez, P. J. Campos, and G. Asensio, “A General and Useful Copper(II)-Promoted Iodofunctionalization of Unsaturated Systems,” Journal of the Chemical Society, Chemical Communications 19, no. 19 (1987): 1491–2.
   Google Scholar
• C. A. Horiuchi, A. Ikeda, M. Kanamori, H. Hosokawa, T. Sugiyama, and T. T. Takahashi, “A New Synthesis of Trans-Iodohydrins UsingIodine–Cerium(IV) Salts,” Journal of Chemical Research no. 2 (1997) : 60–1.
   Web of Science ®Google Scholar
• C. A. Horiuchi, Y. Saitoh, T. Utsukihara, S. Takahashi, M. Matsushita, L. He, T. T. Takahashi, C. Hashimoto, T. Sugiyama, and S. Nozaki, “Reaction of α,Β‐Unsaturated Ketones with Cerium(IV) Salts in Alcohol,” Applied Organometallic Chemistry 20, no. 10 (2006): 663–8.
   Web of Science ®Google Scholar
• R. Antonioletti, M. D'Auria, A. De Mico, G. Piancatelli, and A. Scettri, “A Facile Route to Iodohydrins and Epoxides by Oxidation of Olefin-Iodine Complexes with Pyridinium Dichromate,” Tetrahedron 39, no. 10 (1983): 1765–8.
   Web of Science ®Google Scholar
• K. Miyata, S. Yasuda, T. Masuya, S. Ito, Y. Kinoshita, H. Tamiaki, and T. Oba, “Facile Iodination of the Vinyl Groups in Protoporphyrin IX Dimethyl Ester and Subsequent Transformation of the Iodinated Moieties,” Tetrahedron 74, no. 27 (2018): 3707–11.
   Web of Science ®Google Scholar
• G. Asensio, C. Andreu, C. Boix-Bernardini, R. Mello, and M. E. González-Nuñez, “Iodomethane Oxidation by Dimethyldioxirane: A New Route to Hypoiodous Acid and Iodohydrines,” Organic Letters 1, no. 13 (1999): 2125–8.
   Web of Science ®Google Scholar
• C. R. LeBlond, K. Rossen, F. P. Gortsema, I. A. Zavialov, S. J. Cianciosi, A. T. Andrews, and Y. Sun, “Harvesting Short-Lived Hypoiodous Acid for Efficient Diastereoselective Iodohydroxylation in Crixivan Synthesis,” Tetrahedron Letters 42, no. 49 (2001): 8603–6.
   Web of Science ®Google Scholar
• N. Chakraborty, S. Santra, S. K. Kundu, A. Hajra, G. V. Zyryanov, and A. Majee, “Combination of NH2OH.HCl and NaIO4: An Effective Reagent for Molecular Iodine-Free Regioselective 1,2-Difunctionalization of Olefins and Easy Access of Terminal Acetal,” RSC Advances 5, no. 70 (2015): 56780–8.
   Web of Science ®Google Scholar
• D. S. Rao, T. R. Reddy, K. Babachary, and S. Kashyap, “Regioselective Vicinal Functionalization of Unactivated Alkenes with Sulfonium Iodate(I) Reagents under Metal-Free Conditions,” Organic & Biomolecular Chemistry 14, no. 31 (2016): 7529–43.
   PubMed Web of Science ®Google Scholar
• H. Masuda, K. Takase, M. Nishio, A. Hasegawa, Y. Nishiyama, and Y. Ishii, “A New Synthetic Method of Preparing Iodohydrin and Bromohydrin Derivatives through in Situ Generation of Hypohalous Acids from H5IO6 and NaBrO3 in the Presence of NaHSO3,” The Journal of Organic Chemistry 59, no. 19 (1994): 5550–5.
   Web of Science ®Google Scholar
• S. Hajra, A. Karmakar, and M. Bhowmick, “Silver(I)-Promoted Asymmetric Halohydrin Reaction of Chiral N-Enoyl-2-Oxazolidinones: Scope and Limitations,” Tetrahedron 61, no. 9 (2005): 2279–86.
   Web of Science ®Google Scholar
• A. R. De Corso, B. Panunzi, and M. Tingoli, “Iodohydroxylation of Alkenes Promoted by Molecular and Hypervalent(III) Iodine,” Tetrahedron Letters 42, no. 41 (2001): 7245–7.
   Web of Science ®Google Scholar
• J.-M Chen L.-L. Wu, and X. Huang, “An Efficient Route to Iodohydrin Using Polymer-Supported Hypervalent Iodine(III) Reagent,”Chinese Chemical Letters 15, (2004): 1387–8.
   Web of Science ®Google Scholar
• C. Fu, G. Chen, X. Liu, and S. Ma, “Stereoselective Z-Iodoalkoxylation of 1,2-Allenyl Sulfides or Selenides,” Tetrahedron 61, no. 32 (2005): 7768–73.
   Web of Science ®Google Scholar
• Z. Gu, Y. Deng, W. Shu, and S. Ma, “Highly Regio‐and Stereoselective Iodohydroxylation of Non‐Heteroatom‐Substituted Allenes: An Efficient Synthesis of 4‐[3′‐Hydroxy‐2′‐Iodoalk‐1′(Z)‐Enyl]‐2 (5H)‐Furanone Derivatives,” Advanced Synthesis & Catalysis 349, (2007): 1653–6.
   Web of Science ®Google Scholar
• B. Borhan, S. Nazarian, E. M. Stocking, B. D. Hammock, and M. J. Kurth, “An Efficient Preparation of 18O-Labeled Epoxides,” The Journal of Organic Chemistry 59, no. 15 (1994): 4316–8.
   Web of Science ®Google Scholar
• M. De Castro, and C. H. Marzabadi, “The Preparation of 2-Iodoamides from Glucals and Their Further Transformations into Oxazolines,” Tetrahedron Letters 45, no. 34 (2004): 6501–4.
   Web of Science ®Google Scholar
• R. A. S. Villegas, E. Santo, Jr M. Mattos, M. R. M. P. de Aguiar, and A. W. S. Guarino, “Characterization of Natural Brazilian Clays and Their Utilization as Catalysts in the Coiodination of Alkenes with Water and Alcohols,” Journal of the Brazilian Chemical Society 16, no. 3b (2005): 565–70.
   Web of Science ®Google Scholar
• A. M. Sanseverino, and M. C. S. de Mattos, “Iodohydrins: An Easy Route to Epoxides from Alkenes,” Synthetic Communications 28, no. 3 (1998): 559–72.
   Web of Science ®Google Scholar
• R. A. S. Villegas, M. R. M. P. de Aguiar, M. Mattos, A. W. S. Guarino, L. M. Barbosa, and L. C. F. N. Assumpção, “An Environmentally Friendly Preparation of Iodohydrins from Alkenes Mediated by Clay-Minerals,” Journal of the Brazilian Chemical Society 15, no. 1 (2004): 150–2.
   Web of Science ®Google Scholar
• I. Carrera, M. C. Brovetto, and G. A. Seoane, “Selenium-Catalyzed Iodohydrin Formation from Alkenes,” Tetrahedron Letters 47, no. 45 (2006): 7849–52.
   Web of Science ®Google Scholar
• S. Adimurthy, G. Ramachandraiah, and P. K. Ghosh, “I−/IO3− Assemblies as Promoters of Iodohydrin Formation,” Synthetic Communications 37, no. 9 (2007): 1579–85.
   Web of Science ®Google Scholar
• R. da S. Ribeiro, P. M. Esteves, and M. C. S. de Mattos, “Triiodoisocyanuric Acid: A New and Convenient Reagent for Regioselective Coiodination of Alkenes and Enolethers with Oxygenated Nucleophiles,” Tetrahedron Letters 48, no. 49 (2007): 8747–51.
   Web of Science ®Google Scholar
• J. S. Yadav, B. V. S. Reddy, G. Baishya, S. J. Harshavardhan, C. J. Chary, and M. K. Gupta, “Green Approach for the Conversion of Olefins into Vic-Halohydrins Using N-Halosuccinimides in Ionic Liquids,” Tetrahedron Letters 46, no. 20 (2005): 3569–72.
   Web of Science ®Google Scholar
• M. Narender, M. S. Reddy, Y. V. D. Nageswar, and K. R. Rao, “Aqueous Phase Synthesis of Vic-Halohydrins from Olefins and N-Halosuccinimides in the Presence of β-Cyclodextrin,” Journal of Molecular Catalysis A: Chemical 258, no. 1–2 (2006): 10–4.
   Google Scholar
• B. Das, K. Venkateswarlu, K. Damodar, and K. Suneel, “Ammonium Acetate Catalyzed Improved Method for the Regioselective Conversion of Olefins into Halohydrins and Haloethers at Room Temperature,” Journal of Molecular Catalysis A: Chemical 269, no. 1-2 (2007): 17–21.
   Google Scholar
• K. S. M. Corrêa, R. B. Bernini, M. Mattos, M. R. M. P. de Aguiar, and A. W. S. Guarino, “A New Environmental Friendly Clay Catalyst for One-Pot Coiodination and Epoxidation of Alkenes,” Journal of the Brazilian Chemical Society 18, no. 8 (2007): 1509–14.
   Web of Science ®Google Scholar
• J. H. Schauble, E. A. Trauffer, P. P. Deshpande, and R. D. Evans, “Trans Dialkoxylation of Cyclic Alkenes: A Prevost-Type Reaction,” Synthesis 2005, no. 8 (2005): 1333–9.
   Google Scholar