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.
Iuchi
Yosuke
Y
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.
Obora
Yasushi
Y
Ishii
Yasutaka
Y