A Bioinspired Organocatalytic Cascade for the Selective Oxidation of Amines under Air
Résumé
We describe a bioinspired organocatalytic cascade reaction for the selective aerobic oxidative cross-coupling of primary amines to imines. This approach takes advantages of commercially available pyrogallol monomeric precursor to deliver in situ, under air, low loadings of natural purpurogallin. This is further engaged in a catalytic process with the amine substrate affording under single turnover the active biomimetic quinonoid organocatalyst and the homocoupled imine intermediate which is then converted into crosscoupled imine after dynamic transimination. This organocatalytic cascade inspired by both purpurogallin biosynthesis and copper amine oxidases activity allows the aerobic oxidation of non-activated primary amines that non-enzymatic organocatalysts were not able to accomplish alone.
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