Versatile direct dehydrative approach for diaryliodonium(III) salts in fluoroalcohol media.
ABSTRACT We have found that the use of fluoroalcohol media greatly enhanced the efficiency and scope of the direct dehydrative condensation of arenes and hypervalent iodine(III) compounds; the present clean method has a broad range of applicability as well as unique selectivity in the aromatic substrates, and is highly efficient even in polymer functionalization.
Article: Enhanced reactivity of [hydroxy(tosyloxy)iodo]benzene in fluoroalcohol media. Efficient direct synthesis of thienyl(aryl)iodonium salts.[show abstract] [hide abstract]
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.Molecules 01/2010; 15(3):1918-31. · 2.39 Impact Factor