Iron-Catalyzed Highly para-Selective Difluoromethylation of Arenes

Direct functionalization of a C–H bond at either the meta or para position by only changing the catalyst system poses a significant challenge. We herein report the [Fe­(TPP)­Cl]-enabled, selective, C–H difluoromethylation of arenes using BrCF2CO2Et as the difluoromethylation source, which successful...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of the American Chemical Society 2020-12, Vol.142 (49), p.20524-20530
Hauptverfasser: Fan, Wei-Tai, Li, Yuting, Wang, Dongjie, Ji, Shun-Jun, Zhao, Yingsheng
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Direct functionalization of a C–H bond at either the meta or para position by only changing the catalyst system poses a significant challenge. We herein report the [Fe­(TPP)­Cl]-enabled, selective, C–H difluoromethylation of arenes using BrCF2CO2Et as the difluoromethylation source, which successfully altered the selectivity from the meta to the para position. A preliminary mechanistic study revealed the iron porphyrin complex not only activated the aromatic ring but also induced para selectivity due to the influence of ligand sterics.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.0c09545