Oxaziridine-mediated oxygen atom-transfer catalysis: Oxidation of aliphatic C-H bonds

ORGN 419

Benjamin H. Brodsky, bbrodsky@stanford.edu and Justin Du Bois, jdubois@stanford.edu. Department of Chemistry, Stanford University, Stanford, CA 94305
While strategies for the oxidative functionalization of saturated C-H bonds continue to evolve rapidly, a general, catalytic methodology for the selective hydroxylation of aliphatic C-H bonds remains elusive. Using a combination of experimental and theoretical techniques, we have designed, synthesized, and fully characterized a unique class of tricyclic oxaziridine-based oxidants. Unlike most known oxaziridines, these compounds proved capable of O-atom transfer to aliphatic olefins and C-H bonds under mild conditions. In the presence of a suitable co-catalyst and the benign terminal oxidant urea hydrogen peroxide (UHP), these processes are rendered catalytic. Our efforts to develop general oxidative methodology employing this catalytic system will be presented.