Undecorated Cu(OAc)2-Catalyzed C(sp3)-C(sp3) Bond Formation through para-Hydroxy Group Triggered Remote Benzylic C(sp3)-H Bond Functionalization

The undecorated Cu(OAc)2‐catalyzed para‐hydroxy group triggered oxidative coupling of 2,6‐disubstituted 4‐cresols with fluorinated β‐keto esters or malonates leading to benzylic C(sp3)–C(sp3) bond formation was investigated. This formal double C(sp3)–H coupling method features mild conditions, atom...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:European journal of organic chemistry 2015-08, Vol.2015 (24), p.5334-5338
Hauptverfasser: Huang, Jian-Gang, Guo, Ying, Li, Yu-Dan, Liu, Hong-Wei, Liao, Dao-Hua, Ji, Ya-Fei
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The undecorated Cu(OAc)2‐catalyzed para‐hydroxy group triggered oxidative coupling of 2,6‐disubstituted 4‐cresols with fluorinated β‐keto esters or malonates leading to benzylic C(sp3)–C(sp3) bond formation was investigated. This formal double C(sp3)–H coupling method features mild conditions, atom economy, ligand‐ and additive‐free catalysis, and ambient air as the terminal oxidant. This ecofriendly method allows rapid access to highly functionalized 3‐phenylpropanoate derivatives containing fluorinated quaternary carbon‐like centers. On the basis of active p‐benzoquinone methide intermediates, a plausible mechanism was proposed. The Cu(OAc)2‐catalyzed para‐hydroxy group triggered oxidative coupling of 2,6‐disubstituted‐4‐cresols with fluorinated β‐ketone esters or malonates leading to benzylic C(sp3)–C(sp3) bond formation is described with ambient air as the terminal oxidant. Highly functionalized 3‐phenylpropanoate derivatives containing fluorinated quaternary carbon‐like centers are constructed in an ecofriendly manner.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201500706