Mild Method for the Selective Esterification of Carboxylic Acids Based on the Garegg−Samuelsson Reaction

Mild Method for the Selective Esterification of Carboxylic Acids Based on the Garegg−Samuelsson Reaction

A mild method for the selective esterification of primary alcohols is described. The use of different phosphines, I2, and imidazole allows the selective esterification of a wide variety of acids with excellent results. The generation of a bulky phosphonium-carboxylate salt as intermediate could just...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2011-04, Vol.76 (7), p.2277-2281
Hauptverfasser: Morcillo, Sara P, Álvarez de Cienfuegos, Luis, Mota, Antonio J, Justicia, José, Robles, Rafael
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemistry
Carboxylic Acids - chemistry
Catalysis
Chemistry
Esterification
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Imidazoles - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:A mild method for the selective esterification of primary alcohols is described. The use of different phosphines, I2, and imidazole allows the selective esterification of a wide variety of acids with excellent results. The generation of a bulky phosphonium-carboxylate salt as intermediate could justify the selectivity observed in this process. Additionally, amides also can be synthesized with use of this method.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo102395c