Enantioselective N-heterocyclic carbene-catalyzed ß-hydroxylation of enals using nitroarenes: an atom transfer reaction that proceeds via single electron transfer.
J Am Chem Soc
; 136(42): 14674-7, 2014 Oct 22.
Article
em En
| MEDLINE
| ID: mdl-25302860
ABSTRACT
A novel oxidative N-heterocyclic carbene-catalyzed reaction pathway has been discovered. Alkyl and aryl enals undergo ß-hydroxylation via oxygen atom transfer from electron-deficient nitrobenzenes, followed by trapping of the resultant acyl azolium by the solvent. The proposed mechanism involves a single electron transfer event to initiate the reaction followed by radical recombination. This represents a profound mechanistic departure from the established two-electron disconnects in NHC catalysis.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Benzeno
/
Compostos Heterocíclicos
/
Metano
Idioma:
En
Revista:
J Am Chem Soc
Ano de publicação:
2014
Tipo de documento:
Article
País de afiliação:
Estados Unidos