Copper-Catalyzed Oxaziridine-Mediated Oxidation of C–H Bonds

Motiwala, Hashim F.; Gülgeze, Belgin; Aubé, Jeffrey

Copper-Catalyzed Oxaziridine-Mediated Oxidation of C–H Bonds

2012

Motiwala, Hashim F. | Gülgeze, Belgin | Aubé, Jeffrey

The highly regio- and chemoselective oxidation of activated C–H bonds has been observed via copper-catalyzed reactions of oxaziridines. The oxidation proceeded with a variety of substrates, primarily comprising allylic and benzylic examples, as well as one example of an otherwise unactivated tertiary C–H bond. The mechanism of the reaction is proposed to involve single-electron transfer to the oxaziridines to generate a copper-bound radical anion, followed by hydrogen atom abstraction and collapse to products, with regeneration of the catalyst by a final single-electron transfer event. The involvement of allylic radical intermediates was supported by a radical-trapping experiment with TEMPO.

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