Journal of the American Chemical Society, Vol.132, No.8, 2536-2536, 2010
Iridium-Catalyzed alpha-Alkylation of Acetates with Primary Alcohols and Diols
Acetates were successfully alkylated with primary alcohols and alpha,omega-diols in the presence of tert-BuOK Under the influence of [IrCl(cod)](2). For instance, the reaction of tert-butyl acetate with eta-butanol in the presence of tert-BuOK as a base and [IrCl(cod)](2) as a catalyst in tert-BuOH at 100 degrees C produced tert-butyl hexanoate in good yield. When the alpha,omega-diol 1,9-nonanediol was employed, di-tert-butyl tridecanoate was obtained. These reaction,; are the first report of the alkylation of acetates Using alcohols as alkylating agents. This method provides a very convenient direct route to carboxylates, which are very important raw materials in organic and industrial chemistry.