Kinetics and mechanism of PPh3 oxygenation with 3O2 catalyzed by a 1,3,2-oxazaphosphole as flavin mimic

Abstract

A 1,3,2-oxazaphosphole picks up triplet dioxygen in 1 : 1 stoichiometry similar to flavin organic co-factors. 1,3,2-Oxazaphosphole catalyzes the oxygenation of triphenylphosphine to triphenylphosphine oxide. The reaction obeys an overall third order rate equation. In a radical pathway, organic hydroperoxide is formed from the catalyst and ³O₂, which oxygenates PPh₃, similar to flavin cofactors.