C-H Hydroxylation using a Heterocyclic Catalyst

In contrast to the previous highlight, the group of Du Bois at Stanford, USA have concentrated on designing oxaziridine catalysts which can effect similar hydroxylations (Litvinas N D et al, Angew Chem Int Ed, 2009, 48, 4513-6).  The best catalysts are based on the benzoxathiazine ring system, in which the C=N bond is oxidised by hydrogen peroxide to the oxaziridine, and this is the active hydroxylation catalyst.  Some examples are shown below.