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Molecules 2010, 15(3), 1918-1931; doi:10.3390/molecules15031918
Article

Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts

1, 1, 2, 1, 1,2 and 2,*
1 Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, Japan 2 College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga, Japan
* Author to whom correspondence should be addressed.
Received: 3 February 2010 / Revised: 15 March 2010 / Accepted: 16 March 2010 / Published: 17 March 2010
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
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Abstract

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.
Keywords: [hydroxyl(tosyloxy)iodo]benzene; fluoroalcohol solvents; diaryliodonium salts; thiophenes; single-electron-transfer [hydroxyl(tosyloxy)iodo]benzene; fluoroalcohol solvents; diaryliodonium salts; thiophenes; single-electron-transfer
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Ito, M.; Ogawa, C.; Yamaoka, N.; Fujioka, H.; Dohi, T.; Kita, Y. Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts. Molecules 2010, 15, 1918-1931.

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