72862-53-4Relevant academic research and scientific papers
Copper-catalyzed oxaziridine-mediated oxidation of C-H bonds
Motiwala, Hashim F.,Guelgeze, Belgin,Aube, Jeffrey
experimental part, p. 7005 - 7022 (2012/10/08)
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.
