Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions
We report a convenient and practical method for the preparation of nonexplosive cyclic hypervalent iodine(III) oxidants as efficient organocatalysts and reagents for various reactions using Oxone<sup>®</sup> in aqueous solution under mild conditions at room temperature. The thus obtained...
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MDPI AG
2021-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/7/1897 |
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| author | Hideyasu China Nami Kageyama Hotaka Yatabe Naoko Takenaga Toshifumi Dohi |
| author_facet | Hideyasu China Nami Kageyama Hotaka Yatabe Naoko Takenaga Toshifumi Dohi |
| author_sort | Hideyasu China |
| collection | DOAJ |
| description | We report a convenient and practical method for the preparation of nonexplosive cyclic hypervalent iodine(III) oxidants as efficient organocatalysts and reagents for various reactions using Oxone<sup>®</sup> in aqueous solution under mild conditions at room temperature. The thus obtained 2-iodosobenzoic acids (IBAs) could be used as precursors of other cyclic organoiodine(III) derivatives by the solvolytic derivatization of the hydroxy group under mild conditions of 80 °C or lower temperature. These sequential procedures are highly reliable to selectively afford cyclic hypervalent iodine compounds in excellent yields without contamination by hazardous pentavalent iodine(III) compound. |
| first_indexed | 2024-03-10T12:51:33Z |
| format | Article |
| id | doaj.art-afbb680777f84b77a8741543d8923d30 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T12:51:33Z |
| publishDate | 2021-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-afbb680777f84b77a8741543d8923d302023-11-21T13:03:04ZengMDPI AGMolecules1420-30492021-03-01267189710.3390/molecules26071897Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild ConditionsHideyasu China0Nami Kageyama1Hotaka Yatabe2Naoko Takenaga3Toshifumi Dohi4Department of Medical Bioscience, Nagahama Institute of Bio-Science and Technology, 1266, Tamuracho Nagahama-shi, Shiga 526-0829, JapanCollege of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, JapanCollege of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, JapanFaculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku-ku, Nagoya 468-8503, JapanCollege of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, JapanWe report a convenient and practical method for the preparation of nonexplosive cyclic hypervalent iodine(III) oxidants as efficient organocatalysts and reagents for various reactions using Oxone<sup>®</sup> in aqueous solution under mild conditions at room temperature. The thus obtained 2-iodosobenzoic acids (IBAs) could be used as precursors of other cyclic organoiodine(III) derivatives by the solvolytic derivatization of the hydroxy group under mild conditions of 80 °C or lower temperature. These sequential procedures are highly reliable to selectively afford cyclic hypervalent iodine compounds in excellent yields without contamination by hazardous pentavalent iodine(III) compound.https://www.mdpi.com/1420-3049/26/7/1897cyclic organoiodine(III) compoundsOxone<sup>®</sup>water, solvolytic functionalization, mild condition, metal-free, 2-iodosobenzoic acid |
| spellingShingle | Hideyasu China Nami Kageyama Hotaka Yatabe Naoko Takenaga Toshifumi Dohi Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions Molecules cyclic organoiodine(III) compounds Oxone<sup>®</sup> water, solvolytic functionalization, mild condition, metal-free, 2-iodosobenzoic acid |
| title | Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions |
| title_full | Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions |
| title_fullStr | Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions |
| title_full_unstemmed | Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions |
| title_short | Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions |
| title_sort | practical synthesis of 2 iodosobenzoic acid iba without contamination by hazardous 2 iodoxybenzoic acid ibx under mild conditions |
| topic | cyclic organoiodine(III) compounds Oxone<sup>®</sup> water, solvolytic functionalization, mild condition, metal-free, 2-iodosobenzoic acid |
| url | https://www.mdpi.com/1420-3049/26/7/1897 |
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