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 n-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 reactions 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.
Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, High Technology Research Center, and ORDIST, Kansai University, Suita, Osaka 564-8680, Japan.
Yosuke
Y
Iuchi
Yasushi
Y
Obora
Yasutaka
Y
Ishii