Photoinduced Dearomatizing Three‐Component Coupling of Arylphosphines, Alkenes, and Water

A unique photoinduced reaction that couples a triarylphosphine, an alkene, and water to produce 2‐(cyclohexa‐2,5‐dienyl)ethylphosphine oxide is reported herein. The alkene inserts into a C(aryl)−P bond of the arylphosphine, the aryl ring is dearomatized into the cyclohexadienyl ring, and the phospho...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie International Edition 2021-02, Vol.60 (7), p.3551-3555
Hauptverfasser: Masuda, Yusuke, Tsuda, Hiromu, Murakami, Masahiro
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:A unique photoinduced reaction that couples a triarylphosphine, an alkene, and water to produce 2‐(cyclohexa‐2,5‐dienyl)ethylphosphine oxide is reported herein. The alkene inserts into a C(aryl)−P bond of the arylphosphine, the aryl ring is dearomatized into the cyclohexadienyl ring, and the phosphorus is oxidized. The three components are all readily available, and their intermolecular coupling significantly increases molecular complexity. The products formed are applicable to the Wittig olefination. A unique photoinduced reaction that couples a triarylphosphine, an alkene, and water to produce 2‐(cyclohexa‐2,5‐dienyl)ethylphosphine oxide is reported. The three components are all readily available, and their intermolecular coupling significantly increases molecular complexity. The resulting products are applicable to the Wittig olefination.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202013215