Electrophilic organic selenium reagents—protonated seleninic acids as precursors for unsymmetrical aromatic selenides
摘要:
Arylselenylations of methylbenzenes, methoxybenzenes and thiophene were smoothly achieved with selenenium ions generated by comproportionation of 1:1 mixtures of p-toluenesulfonic acid salts of seleninic acids and the corresponding diselenides. A series of p-toluenesulfonic salts of seleninic acids were prepared by hydrogen peroxide oxidation of the corresponding diselenides in the presence of p-toluenesulfonic acid. Novel 2-(organylseleno)thiophenes were obtained by heating the protonated seleninic acids with a 50-fold excess of thiophene in glacial acetic acid. (C) 2011 Published by Elsevier Ltd.
Peraceticacid promoted C–Se coupling reaction of arenes with diselenides under metal-free and solvent-free conditions has been described. The resulting selenide ethers were obtained in good to excellent yields. Peraceticacid provided the selenide ethers via sp 2 C–H selenation whereas previously in case of DTBP sp 3 C–H selenation was observed.