Copper-catalyzed oxaziridine-mediated oxidation of C-H bonds.
J Org Chem
; 77(16): 7005-22, 2012 Aug 17.
Article
em En
| MEDLINE
| ID: mdl-22830300
ABSTRACT
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.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Aziridinas
/
Carbono
/
Cobre
/
Elétrons
/
Hidrogênio
Idioma:
En
Ano de publicação:
2012
Tipo de documento:
Article