CATALYTIC DIOXYGENATION OF CATECHOL BY NON-HEME IRON(III) COMPLEXES AS A SUSTAINABLE ROUTE TO DIMETHYL ADIPATE

摘要

The atom-efficient, direct conversion of functionalized biomass-derived platform molecules to bulk chemicals is an important challenge in the valorization of biomass.1 Catechols constitute an interesting class of renewable platform molecules, as these functionalized aromatics may be obtained from biomass in multiple ways, including fermentation of glucose, pyrolysis of woody biomass or catalytic depolymerization of lignin. In nature, catechols are metabolized by intradiol catechol dioxygenase enzymes, to afford derivatives of cis,cis-muconic acid. Although bio-inspired non-heme iron(III) complexes have been investigated as models for this enzymatic reaction, the catalytic dioxygenation of pyrocatechol using such systems has not received much attention.2 This reaction holds considerable promise, however, as simple hydrogenation of the obtained cis,cis-muconic acid would yield adipic acid, an important bulk chemical consumed on a billion kg/year scale for the production of nylons.