An efficient synthesis of 2-(1-(E)-alkenyl)phenylphosphonates via Suzuki reaction of aryl nonaflates with (E)-1-alkenylboronates

In the presence of Pd(OAc)2, PPh3 and K2CO3, a series of 2-(1-(E)-alkenyl)phenylphosphonates were synthesized efficiently and stereoselectively via the Suzuki reaction of 2-phosphonylaryl nonaflates and (E)-1-alkenylboronic pinacol esters. •An efficient Suzuki reaction has been developed.•A series o...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of fluorine chemistry 2013-07, Vol.151, p.58-62
Hauptverfasser: Peng, Ai-Yun, Chen, Ba-Tian, Chen, Pei-Jiang
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:In the presence of Pd(OAc)2, PPh3 and K2CO3, a series of 2-(1-(E)-alkenyl)phenylphosphonates were synthesized efficiently and stereoselectively via the Suzuki reaction of 2-phosphonylaryl nonaflates and (E)-1-alkenylboronic pinacol esters. •An efficient Suzuki reaction has been developed.•A series of 2-(1-(E)-alkenyl)phenylphosphonates were synthesized.•The reactions are quite general.•The reactions proceed in good yields. An efficient and general Suzuki coupling reaction between 2-phosphonylaryl nonaflates and (E)-1-alkenylboronic pinacol esters using Pd(OAc)2/PPh3 as catalysts, K2CO3 as base and DMF as solvent has been developed. This strategy allows for convenient synthesis of twelve 2-(1-(E)-alkenyl)phenylphosphonates in good to excellent yields, most of which are not readily available by the previously reported Heck reaction of the same aryl nonaflates and terminal alkenes.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2013.03.015