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Iodosobenzene tetrafluoroborate, hexafluoroantimonate, and hexafluorophosphate: stable electrophilic hypervalent iodine reagents without nucleophilic ligands
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    Iodosobenzene tetrafluoroborate, hexafluoroantimonate, and hexafluorophosphate: stable electrophilic hypervalent iodine reagents without nucleophilic ligands
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 1989, 54, 11, 2609–2612
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    https://doi.org/10.1021/jo00272a029
    Published May 1, 1989

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    1. Mio Shimogaki, Morifumi Fujita, and Takashi Sugimura . Enantioselective C–C Bond Formation during the Oxidation of 5-Phenylpent-2-enyl Carboxylates with Hypervalent Iodine(III). The Journal of Organic Chemistry 2017, 82 (22) , 11836-11840. https://doi.org/10.1021/acs.joc.7b01141
    2. Yan-Biao Kang and Lutz H. Gade . Triflic Acid Catalyzed Oxidative Lactonization and Diacetoxylation of Alkenes Using Peroxyacids as Oxidants. The Journal of Organic Chemistry 2012, 77 (3) , 1610-1615. https://doi.org/10.1021/jo202491y
    3. Wenhe Zhong, Jun Yang, Xiangbao Meng, and Zhongjun Li . BF3·OEt2-Promoted Diastereoselective Diacetoxylation of Alkenes by PhI(OAc)2. The Journal of Organic Chemistry 2011, 76 (24) , 9997-10004. https://doi.org/10.1021/jo201752y
    4. Masahito Ochiai,, Kazunori Miyamoto,, Motoo Shiro,, Tomoyuki Ozawa, and, Kentaro Yamaguchi. Isolation, Characterization, and Reaction of Activated Iodosylbenzene Monomer Hydroxy(phenyl)iodonium Ion with Hypervalent Bonding:  Supramolecular Complex PhI+OH·18-Crown-6 with Secondary I···O Interactions. Journal of the American Chemical Society 2003, 125 (43) , 13006-13007. https://doi.org/10.1021/ja0377899
    5. Helen Wilkinson Richter,, Brian R. Cherry,, Teresa D. Zook, and, Gerald F. Koser. Characterization of Species Present in Aqueous Solutions of [Hydroxy(mesyloxy)iodo]benzene and [Hydroxy(tosyloxy)iodo]benzene. Journal of the American Chemical Society 1997, 119 (41) , 9614-9623. https://doi.org/10.1021/ja971751c
    6. Peter J. Stang, , Viktor V. Zhdankin. Organic Polyvalent Iodine Compounds. Chemical Reviews 1996, 96 (3) , 1123-1178. https://doi.org/10.1021/cr940424+
    7. Nicolas G.‐Simonian, Bogdan R. Brutiu, Daniel Kaiser, Nuno Maulide. Kationische, Iod(III)‐vermittelte und dirigierte diastereoselektive Oxidation inerter C−H‐Bindungen in cyclischen Kohlenwasserstoffen. Angewandte Chemie 2025, 137 (13) https://doi.org/10.1002/ange.202421872
    8. Nicolas G.‐Simonian, Bogdan R. Brutiu, Daniel Kaiser, Nuno Maulide. Cationic, Iodine(III)‐Mediated and Directed Diastereoselective Oxidation of Inert C−H Bonds in Cyclic Hydrocarbons. Angewandte Chemie International Edition 2025, 64 (13) https://doi.org/10.1002/anie.202421872
    9. Giulia Iannelli, Philipp Spieß, Ricardo Meyrelles, Daniel Kaiser, Boris Maryasin, Leticia González, Nuno Maulide. Diastereoselective Umpolung cyclisation of ketones promoted by hypervalent iodine. Chemical Science 2025, 18 https://doi.org/10.1039/D5SC01085C
    10. Siddappa Chandrappa, Kereyagalahally H. Narasimhamurthy, Muthipeedika Nibin Joy, Kanchugarakoppal S. Rangappa. One-pot tandem approach for the diastereoselective syn-diacetoxylation of cinnamic esters. Chemical Data Collections 2021, 34 , 100710. https://doi.org/10.1016/j.cdc.2021.100710
    11. Thierry Achard, Stéphane Bellemin‐Laponnaz. Recent Advances on Catalytic Osmium‐Free Olefin syn ‐Dihydroxylation. European Journal of Organic Chemistry 2021, 2021 (6) , 877-896. https://doi.org/10.1002/ejoc.202001209
    12. Xiaojun Deng, Luwen Zhang, Huixia Liu, Yu Bai, Wei He. mCPBA-mediated dioxygenation of unactivated alkenes for the synthesis of 5-imino-2-tetrahydrofuranyl methanol derivatives. Tetrahedron Letters 2020, 61 (50) , 152620. https://doi.org/10.1016/j.tetlet.2020.152620
    13. Xin Huang, Yage Zhang, Chaoshen Zhang, Lei Zhang, Ying Xu, Lichun Kong, Zhi‐Xiang Wang, Bo Peng. The ortho ‐Difluoroalkylation of Aryliodanes with Enol Silyl Ethers: Rearrangement Enabled by a Fluorine Effect. Angewandte Chemie 2019, 131 (18) , 6017-6022. https://doi.org/10.1002/ange.201900745
    14. Xin Huang, Yage Zhang, Chaoshen Zhang, Lei Zhang, Ying Xu, Lichun Kong, Zhi‐Xiang Wang, Bo Peng. The ortho ‐Difluoroalkylation of Aryliodanes with Enol Silyl Ethers: Rearrangement Enabled by a Fluorine Effect. Angewandte Chemie International Edition 2019, 58 (18) , 5956-5961. https://doi.org/10.1002/anie.201900745
    15. Chuan Wang. Vicinal anti ‐Dioxygenation of Alkenes. Asian Journal of Organic Chemistry 2018, 7 (3) , 509-521. https://doi.org/10.1002/ajoc.201700621
    16. Richard C. Larock, Tanay Kesharwani. Formation of Ethers by Alkane, Arene, Alkene, and Alkyne Substitutions and Additions. 2018, 11-104. https://doi.org/10.1002/9781118662083.cot06-003
    17. Richard C. Larock, Anton V. Dubrovskiy, Nataliya A. Markina. Alkylation and Acylation of Aldehydes, Ketones, and Their Derivatives. 2018, 1-145. https://doi.org/10.1002/9781118662083.cot08-013
    18. Keshaba N Parida, Gulab K Pathe, Shimon Maksymenko, Alex M Szpilman. Cross-coupling of dissimilar ketone enolates via enolonium species to afford non-symmetrical 1,4-diketones. Beilstein Journal of Organic Chemistry 2018, 14 , 992-997. https://doi.org/10.3762/bjoc.14.84
    19. Richard C. Larock, Tuanli Yao. Formation of Nitriles, Carboxylic Acids, and Derivatives by Oxidation, Substitution, and Addition. 2017, 1-85. https://doi.org/10.1002/9781118662083.cot09-001
    20. Antoine Jobin‐Des Lauriers, Claude Y. Legault. Enol and Ynol Surrogates: Promising Substrates for Hypervalent Iodine Chemistry. Asian Journal of Organic Chemistry 2016, 5 (9) , 1078-1099. https://doi.org/10.1002/ajoc.201600246
    21. Yan-Biao Kang, Xian-Min Chen, Chuan-Zhi Yao, Xiao-Shan Ning. Direct oxidative lactonization of alkenoic acids mediated solely by NaIO 4 : beyond a simple oxidant. Chemical Communications 2016, 52 (36) , 6193-6196. https://doi.org/10.1039/C6CC02246D
    22. Mio Shimogaki, Morifumi Fujita, Takashi Sugimura. Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III). Molecules 2015, 20 (9) , 17041-17057. https://doi.org/10.3390/molecules200917041
    23. Pushpak Mizar, Thomas Wirth. Flexible stereoselektive Funktionalisierung von Ketonen durch Umpolung mit hypervalenten Iodreagentien. Angewandte Chemie 2014, 126 (23) , 6103-6107. https://doi.org/10.1002/ange.201400405
    24. Pushpak Mizar, Thomas Wirth. Flexible Stereoselective Functionalizations of Ketones through Umpolung with Hypervalent Iodine Reagents. Angewandte Chemie International Edition 2014, 53 (23) , 5993-5997. https://doi.org/10.1002/anie.201400405
    25. Luke I. Dixon, Michael A. Carroll*, George J. Ellames, Thomas J. Gregson. Synthesis of Alkynyliodonium Salts: Preparation of Phenyl(phenylethynyl)iodonium Trifluoroacetate. 2014, 60-71. https://doi.org/10.1002/0471264229.os091.06
    26. F.V. Singh, T Wirth. 7.29 Oxidative Functionalization with Hypervalent Halides. 2014, 880-933. https://doi.org/10.1016/B978-0-08-097742-3.00735-7
    27. . Preparation, Structure and Properties of Polyvalent Iodine Compounds. 2013, 21-143. https://doi.org/10.1002/9781118341155.ch2
    28. Luke I. Dixon, Michael A. Carroll, Thomas J. Gregson, George J. Ellames, Ross W. Harrington, William Clegg. Synthesis and Reactivity of Aryl(alkynyl)iodonium Salts. European Journal of Organic Chemistry 2013, 2013 (12) , 2334-2345. https://doi.org/10.1002/ejoc.201300092
    29. Michael J. Rawling, Nicholas C. O. Tomkinson. Metal-free syn-dioxygenation of alkenes. Organic & Biomolecular Chemistry 2013, 11 (9) , 1434. https://doi.org/10.1039/c3ob27387c
    30. Luke I. Dixon, Michael A. Carroll, Thomas J. Gregson, George J. Ellames, Ross W. Harrington, William Clegg. Unprecedented regiochemical control in the formation of aryl[1,2-a]imidazopyridines from alkynyliodonium salts: mechanistic insights. Organic & Biomolecular Chemistry 2013, 11 (35) , 5877. https://doi.org/10.1039/c3ob41112e
    31. Kelly E. Lutz, Regan J. Thomson. A Hypervalent Iodide‐Initiated Fragment Coupling Cascade of N ‐Allylhydrazones. Angewandte Chemie 2011, 123 (19) , 4529-4532. https://doi.org/10.1002/ange.201100888
    32. Kelly E. Lutz, Regan J. Thomson. A Hypervalent Iodide‐Initiated Fragment Coupling Cascade of N ‐Allylhydrazones. Angewandte Chemie International Edition 2011, 50 (19) , 4437-4440. https://doi.org/10.1002/anie.201100888
    33. Morifumi Fujita, Mikimasa Wakita, Takashi Sugimura. Enantioselective Prévost and Woodward reactions using chiral hypervalent iodine(iii): switchover of stereochemical course of an optically active 1,3-dioxolan-2-yl cation. Chemical Communications 2011, 47 (13) , 3983. https://doi.org/10.1039/c1cc10129c
    34. Kallol Ray, Jason England, Adam T. Fiedler, Marlène Martinho, Eckard Münck, Lawrence Que. An Inverted and More Oxidizing Isomer of [Fe IV (O)(tmc)(NCCH 3 )] 2+. Angewandte Chemie 2008, 120 (42) , 8188-8191. https://doi.org/10.1002/ange.200802219
    35. Kallol Ray, Jason England, Adam T. Fiedler, Marlène Martinho, Eckard Münck, Lawrence Que. An Inverted and More Oxidizing Isomer of [Fe IV (O)(tmc)(NCCH 3 )] 2+. Angewandte Chemie International Edition 2008, 47 (42) , 8068-8071. https://doi.org/10.1002/anie.200802219
    36. E. D. Matveeva, T. A. Podrugina, Yu. K. Grishin, A. S. Pavlova, N. S. Zefirov. Phosphonium-iodonim ylides in nucleophilic substitution reactions. Russian Journal of Organic Chemistry 2007, 43 (2) , 201-206. https://doi.org/10.1134/S107042800702008X
    37. Masahito Ochiai. Stoichiometric and catalytic oxidations with hypervalent organo‐λ 3 ‐iodanes. The Chemical Record 2007, 7 (1) , 12-23. https://doi.org/10.1002/tcr.20104
    38. Jie Yan. A Catalyst- and Solvent-Free Suzuki Coupling Reaction of Sodium Tetraphenylborate with Hypervalent Iodanes. Journal of Chemical Research 2006, 2006 (7) , 459-460. https://doi.org/10.3184/030823406777980600
    39. Jie Yan, Zhongshi Zhou, Min Zhu. Rapid Microwave‐Promoted Base‐Free Suzuki Coupling Reaction of Sodium Tetraphenylborate with Hypervalent Iodonium Compounds in Water. Synthetic Communications 2006, 36 (11) , 1495-1502. https://doi.org/10.1080/00397910600588454
    40. Luiz F. Silva. Hypervalent Iodine–Mediated Ring Contraction Reactions. Molecules 2006, 11 (6) , 421-434. https://doi.org/10.3390/11060421
    41. Jie Yan, Min Zhu, Zhongshi Zhou. Rapid Microwave‐Promoted Catalyst‐ and Base‐Free Suzuki‐Type Coupling Reaction in Water. European Journal of Organic Chemistry 2006, 2006 (9) , 2060-2062. https://doi.org/10.1002/ejoc.200500915
    42. Murat Çelik, Cemalettin Alp, Betül Coşkun, M. Serdar Gültekin, Metin Balci. Synthesis of diols using the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate). Tetrahedron Letters 2006, 47 (22) , 3659-3663. https://doi.org/10.1016/j.tetlet.2006.03.137
    43. Nathalie Lebrasseur, Gao-Jun Fan, Mayalen Oxoby, Matthew A. Looney, Stéphane Quideau. λ3-Iodane-mediated arenol dearomatization. Synthesis of five-membered ring-containing analogues of the aquayamycin ABC tricyclic unit and novel access to the apoptosis inducer menadione. Tetrahedron 2005, 61 (6) , 1551-1562. https://doi.org/10.1016/j.tet.2004.11.072
    44. Anastasios Varvoglis. Preparation of Hypervalent Iodine Compounds. 2003, 69-98. https://doi.org/10.1007/3-540-46114-0_3
    45. Kenji Kobayashi, Kunimasa Tanaka, Hiroyuki Izawa, Yoriko Arai, Naomichi Furukawa. Syntheses and Properties of Ditelluroxanes and Oligochalcogenoxanes: Hypervalent Oligomers with Te−O Apical Linkages in the Main Chain. Chemistry - A European Journal 2001, 7 (19) , 4272-4279. https://doi.org/10.1002/1521-3765(20011001)7:19<4272::AID-CHEM4272>3.0.CO;2-U
    46. Valery K Brel, Namig Sh Pirkuliev, Nikolai S Zefirov. Chemistry of xenon derivatives. Synthesis and chemical properties. Russian Chemical Reviews 2001, 70 (3) , 231-264. https://doi.org/10.1070/RC2001v070n03ABEH000626
    47. Robert M. Moriarty, Om Prakash. Oxidation of Carbonyl Compounds with Organohypervalent Iodine Reagents. 1999, 273-418. https://doi.org/10.1002/0471264180.or054.02
    48. . Chapter 5 Ligand coupling involving organoiodine compounds. 1998, 107-158. https://doi.org/10.1016/S1460-1567(98)80020-2
    49. Antonella De Mico, Roberto Margarita, Luca Parlanti, Giovanni Piancatelli, Andrea Vescovi. Hypervalent iodine induced nucleophilic additions to alkenes: Synthesis of 1,2-diperchlorates. Tetrahedron 1997, 53 (49) , 16877-16882. https://doi.org/10.1016/S0040-4020(97)10122-3
    50. Takhar M Kasumov, Anatolii S Koz'min, Nikolai S Zefirov. Chemistry of inorganic sulfonates and sulfates of polyvalent iodine. Russian Chemical Reviews 1997, 66 (10) , 843-857. https://doi.org/10.1070/RC1997v066n10ABEH000282
    51. Tsugio Kitamura, Yuzo Fujiwara. RECENT PROGRESS IN THE USE OF HYPERVALENT IODINE REAGENTS IN ORGANIC SYNTHESIS. A REVIEW. Organic Preparations and Procedures International 1997, 29 (4) , 409-458. https://doi.org/10.1080/00304949709355217
    52. A. Varvoglis. Some Further Reagents of lodine(III). 1997, 211-218. https://doi.org/10.1016/B978-012714975-2/50014-4
    53. Anastasios Varvoglis. Chemical transformations induced by hypervalent iodine reagents. Tetrahedron 1997, 53 (4) , 1179-1255. https://doi.org/10.1016/S0040-4020(96)00970-2
    54. Viktor V. Zhdankin, Chris J. Kuehl, Angela J. Simonsen. Iodosylperfluoroalkanes as Reagents for the Preparation of Perfluoroalkyliodonium Salts under Aprotic Conditions. Main Group Chemistry 1996, 1 (3) , 349-352. https://doi.org/10.1080/13583149612331338657
    55. Om Prakash, Neena Saini, Madan P. Tanwar, Robert M. Moriarty. Hypervalent iodine in organic synthesis: α-functionalization of carbonyl compounds. Contemp. Org. Synth. 1995, 2 (2) , 121-131. https://doi.org/10.1039/CO9950200121
    56. Kenneth K. Laali. Probing onium ions and carbocations by desorption/ionization mass spectrometry: Crossing the threshold between fragile salts and gaseous intact cations and subsequent guest–host and cation–molecule cluster chemistry. Journal of Physical Organic Chemistry 1994, 7 (9) , 465-478. https://doi.org/10.1002/poc.610070902
    57. Viktor V. Zhdankin, Chris Kuehl. [Hydroxy(sulfonyloxy)iodo]perfluoroalkanes - new hypervalent iodine species and promising reagents for organic synthesis. Tetrahedron Letters 1994, 35 (12) , 1809-1812. https://doi.org/10.1016/S0040-4039(00)73166-2
    58. Gerhard Maas, Antonio Fronda. Oxidative Desilylation of a 5,6:7,8‐Bis(dimethylsilyldioxy)[4]radialene. Chemische Berichte 1993, 126 (2) , 523-527. https://doi.org/10.1002/cber.19931260232
    59. Peter J. Stang. Alkinyl‐ und Alkenyl(phenyl)iodoniumverbindungen. Angewandte Chemie 1992, 104 (3) , 281-292. https://doi.org/10.1002/ange.19921040306
    60. Peter J. Stang. Alkynyl‐ and Alkenyl(phenyl)iodonium Compounds. New Synthetic Methods (86). Angewandte Chemie International Edition in English 1992, 31 (3) , 274-285. https://doi.org/10.1002/anie.199202741
    61. Marcello Tiecco, Lorenzo Testaferri, Marco Tingoli, Donatella Bartoli. Iodine (III) mediated acetoxy-lactonization of unsaturated nitriles. Tetrahedron 1990, 46 (20) , 7139-7150. https://doi.org/10.1016/S0040-4020(01)87896-0
    62. Valery K. Brel, Anatoly S. Koz'min, Ivan V. Martynov, Viktor I. Uvarov, Nikolai S. Zefirov, Viktor V. Zhdankin, Peter J. Stang. Introduction of the halonitromethyl framework into aromatic rings via a XeF2 mediated radical process. Tetrahedron Letters 1990, 31 (33) , 4799-4800. https://doi.org/10.1016/S0040-4039(00)97737-2
    63. Valery K. Brel, Anatoly S. Koz'min, Viktor I. Uvarov, Nikolai S. Zefirov, Viktor V. Zhdankin, Peter J. Stang. Xenon fluorosulfates and their AdE-reactions with olefins. Tetrahedron Letters 1990, 31 (36) , 5225-5226. https://doi.org/10.1016/S0040-4039(00)97849-3
    64. V. V. ZHDANKIN, R. TYKWINSKI, B. BERGLUND, M. MULLIKIN, R. CAPLE, N. S. ZEFIROV, A. S. KOZ'MIN. ChemInform Abstract: Iodosobenzene Tetrafluoroborate, Hexafluoroantimonate, and Hexafluorophosphate: Stable Electrophilic Hypervalent Iodine Reagents Without Nucleophilic Ligands.. ChemInform 1989, 20 (47) https://doi.org/10.1002/chin.198947141

    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 1989, 54, 11, 2609–2612
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo00272a029
    Published May 1, 1989

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