Oxidation of thiols to disulfides by dioxygen catalyzed by a bioinspired organocatalyst

Abstract

2,3-Dihydro-2,2,2-triphenylphenanthro[9,10-d]-1,3,2-λ⁵-oxazaphosphole serves as good catalyst for the oxidation of thiophenol, cysteine and glutathione to their disulfides by molecular oxygen. The kinetics of the reactions unveiled an overall second order rate equation for all reactions and pure dioxygen chemistry for all three substrates. The formation of an unstable hydroperoxide from the catalyst is assumed to be a key step during the reaction.