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

Autor:	Toshifumi Dohi, Hiromichi Fujioka, Chieko Ogawa, Nobutaka Yamaoka, Motoki Ito, Yasuyuki Kita
Jazyk:	angličtina
Rok vydání:	2010
Předmět:	[hydroxyl(tosyloxy)iodo]benzene fluoroalcohol solvents diaryliodonium salts thiophenes single-electron-transfer Organic chemistry QD241-441
Zdroj:	Molecules, Vol 15, Iss 3, Pp 1918-1931 (2010)
Druh dokumentu:	article
ISSN:	15031918 1420-3049
DOI:	10.3390/molecules15031918
Popis:	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.
Databáze:	Directory of Open Access Journals
Externí odkaz:	https://doaj.org/article/388311b092af426c8d76a797db7c3d32 Zobrazit plný text záznamu View record in DOAJ Plný text ve formátu PDF