Nucleophilic fluorination of triflates by tetrabutylammonium bifluoride.
J Org Chem
; 73(20): 8106-8, 2008 Oct 17.
Article
en En
| MEDLINE
| ID: mdl-18808183
Careful examination of nucleophilicity, basicity, and leaving group ability led us to discover the nucleophilic fluorination of triflates by weakly basic tetrabutylammonium bifluoride, which provides excellent yields with minimal formation of elimination-derived side products. Primary hydroxyl groups as well as secondary hydroxyl groups in acyclic chains or in five-membered rings are excellent substrates, whereas benzylic and aldol-type secondary hydroxyl groups give poor yields as a result of the instability of their triflates.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Compuestos de Amonio Cuaternario
Idioma:
En
Revista:
J Org Chem
Año:
2008
Tipo del documento:
Article
Pais de publicación:
Estados Unidos