Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts
In this manuscript, we report clear evidence for the generation of aromatic cation radicals produced by using [hydroxy(tosyloxy)iodo]benzene (HTIB) in fluoroalcohol solvents such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). The single-electron-transfer (SET) oxidatio...
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| Format: | Article |
| Language: | English |
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MDPI AG
2010-03-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/15/3/1918/ |
| _version_ | 1818483653349474304 |
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| author | Toshifumi Dohi Hiromichi Fujioka Chieko Ogawa Nobutaka Yamaoka Motoki Ito Yasuyuki Kita |
| author_facet | Toshifumi Dohi Hiromichi Fujioka Chieko Ogawa Nobutaka Yamaoka Motoki Ito Yasuyuki Kita |
| author_sort | Toshifumi Dohi |
| collection | DOAJ |
| description | In this manuscript, we report clear evidence for the generation of aromatic cation radicals produced by using [hydroxy(tosyloxy)iodo]benzene (HTIB) in fluoroalcohol solvents such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). The single-electron-transfer (SET) oxidation ability of HTIB to give cation radicals was first established by ESR and UV measurements. The reaction was broadly applied to various thiophenes, and unique thienyliodonium salts were directly synthesized by this method in excellent yields without the production of any harmful byproducts. |
| first_indexed | 2024-12-10T15:44:44Z |
| format | Article |
| id | doaj.art-388311b092af426c8d76a797db7c3d32 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-10T15:44:44Z |
| publishDate | 2010-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-388311b092af426c8d76a797db7c3d322022-12-22T01:42:59ZengMDPI AGMolecules1420-30492010-03-011531918193110.3390/molecules15031918Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium SaltsToshifumi DohiHiromichi FujiokaChieko OgawaNobutaka YamaokaMotoki ItoYasuyuki KitaIn this manuscript, we report clear evidence for the generation of aromatic cation radicals produced by using [hydroxy(tosyloxy)iodo]benzene (HTIB) in fluoroalcohol solvents such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). The single-electron-transfer (SET) oxidation ability of HTIB to give cation radicals was first established by ESR and UV measurements. The reaction was broadly applied to various thiophenes, and unique thienyliodonium salts were directly synthesized by this method in excellent yields without the production of any harmful byproducts.http://www.mdpi.com/1420-3049/15/3/1918/[hydroxyl(tosyloxy)iodo]benzenefluoroalcohol solventsdiaryliodonium saltsthiophenessingle-electron-transfer |
| spellingShingle | Toshifumi Dohi Hiromichi Fujioka Chieko Ogawa Nobutaka Yamaoka Motoki Ito Yasuyuki Kita Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts Molecules [hydroxyl(tosyloxy)iodo]benzene fluoroalcohol solvents diaryliodonium salts thiophenes single-electron-transfer |
| title | Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts |
| title_full | Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts |
| title_fullStr | Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts |
| title_full_unstemmed | Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts |
| title_short | Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts |
| title_sort | enhanced reactivity of hydroxy tosyloxy iodo benzene in fluoroalcohol media efficient direct synthesis of thienyl aryl iodonium salts |
| topic | [hydroxyl(tosyloxy)iodo]benzene fluoroalcohol solvents diaryliodonium salts thiophenes single-electron-transfer |
| url | http://www.mdpi.com/1420-3049/15/3/1918/ |
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