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

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-H-2), i.e. Mg(PBTP) and Na-2(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.

Automated summary

This study developed magnesium(ii) and sodium(i) complexes derived from BHT-H and PBTP-H-2 as catalysts for the transesterification of MA and MMA. The Mg(PBTP) and Na-2(PBTP) catalysts were found to be 41 and 81 times more effective than Mg(BHT)(2) and Na(BHT), respectively. These catalysts showed high efficiency across a range of alcohols.