Bulky magnesium(ii) and sodium(i) bisphenoxide catalysts for chemoselective transesterification of methyl (meth)acrylates

Abstract

Given the industrial importance of (meth)acrylate esters, various groups have devoted considerable effort to investigating their chemoselective transesterification. In 2021, we developed magnesium(II) and sodium(I) complexes derived from 2,6-di-tert-butyl-p-cresol (BHT-H) as chemoselective catalysts for the transesterification of methyl acrylate (MA) and methyl methacrylate (MMA), respectively. Based on our results, we report the discovery of magnesium(II) and sodium(I) salts derived from 6,6′-(propane-2,2′-diyl)bis(2,4-di-tert-butylphenol) (PBTP-H₂), i.e. Mg(PBTP) and Na₂(PBTP), which are 41 and 81 times more effective catalysts than Mg(BHT)₂ and Na(BHT) for the transesterification of MA and MMA, respectively. These new catalysts are highly effective across an extensive range of alcohols, including primary and secondary alcohols, diols, and triols. Overall, this efficient transesterification technology can be expected to find practical applications in industrial process chemistry.