Carbonylation of Difluoroalkyl Bromides Catalyzed by Palladium

Although important progress has been made in the fluoroalkylation reactions, the transition‐metal‐catalyzed carbonylative fluoroalkylation reaction remains challenging so far. Herein, we report the first example of a Pd‐catalyzed carbonylation of difluoroalkyl bromides with (hetero)arylboronic acids...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie International Edition 2016-08, Vol.55 (35), p.10401-10405
Hauptverfasser: Zhao, Hai-Yang, Feng, Zhang, Luo, Zhiji, Zhang, Xingang
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Although important progress has been made in the fluoroalkylation reactions, the transition‐metal‐catalyzed carbonylative fluoroalkylation reaction remains challenging so far. Herein, we report the first example of a Pd‐catalyzed carbonylation of difluoroalkyl bromides with (hetero)arylboronic acids under one atmosphere pressure of CO. The reaction can also be extended to the aryl potassium trifluoroborate salts. The advantages of this protocol are synthetic simplicity, broad substrate scope, and excellent functional group compatibility. The resulting difluoroalkyl ketones can serve as versatile building blocks for the synthesis of various useful fluorinated compounds. Insertion of CO: A palladium‐catalyzed carbonylation reaction of difluoroalkyl halides into ketones was developed (see picture). The resulting difluoroalkyl ketones can serve as versatile building blocks for the synthesis of useful fluorinated compounds.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201605380