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DOI: 10.1055/s-0029-1217585
Organocatalytic C-H Hydroxylation
N. D. Litvinas, B. H. Brodsky, J. Du Bois*
Stanford University, USA
Publikationsverlauf
Publikationsdatum:
23. Juli 2009 (online)

Significance
Based on the authors’ previous work in this field (J. Am. Chem. Soc. 2005, 127, 15391) a second-generation oxaziridine 2-mediated catalytic process for C-H hydroxylation is reported. The revised reaction protocol features the use of aqueous H2O2 in AcOH-H2O (1:1), conditions which efficiently generate the reactive oxaziridine intermediate 2 in situ from the benzoxathiazine catalyst 1. Among all catalysts 1 tested, catalyst 1e (R = C6F5) turned out to be the most effective suggesting hydrophobic catalyst-substrate aggregation as proposed by the authors. Mechanistically, oxaziridine-mediated electrophilic O-atom insertion into C-H bonds likely proceeds in a concerted, asynchronous fashion.