Extradiol oxygenation of 3,5-di-tert-butylcatechol with O2by iron chlorides in tetrahydrofuran–water as a model reaction for catechol-2,3-dioxygenases

Abstract

Selective extradiol oxygenation of 3,5-di-tert-bytylcatechol 1 with O₂catalysed by Fe²⁺ is achieved in THF in the presence of water; the different selectivity obtained by FeCl₂ and FeCl₃ in THF–H₂O and THF–pyridine supports the explanation of the intra- and extra-diol oxygenations by Fe³⁺ and Fe²⁺, respectively, as proposed in the enyzmatic systems.