Rhodium-Catalyzed Acyl-Transfer Reaction between Benzyl Ketones and Thioesters: Synthesis of Unsymmetric Ketones by Ketone CO–C Bond Cleavage and Intermolecular Rearrangement

In the presence of catalytic amounts of RhH(CO)(PPh3)3 and 1,2-bis(diphenylphosphino)benzene (dppBz), acyl groups were transferred between benzyl ketones and thioesters/aryl esters. The rhodium complex catalyzed the cleavage of ketone CO–C bonds and intermolecular rearrangement giving unsymmetric ke...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Organic letters 2012-07, Vol.14 (14), p.3804-3807
Hauptverfasser:	Arisawa, Mieko, Kuwajima, Manabu, Toriyama, Fumihiko, Li, Guangzhe, Yamaguchi, Masahiko
Format:	Artikel
Sprache:	eng
Schlagworte:	Benzene Derivatives - chemical synthesis Benzene Derivatives - chemistry Catalysis Esters Ketones - chemical synthesis Ketones - chemistry Molecular Structure Nitriles - chemical synthesis Nitriles - chemistry Organophosphonates - chemical synthesis Organophosphonates - chemistry Propane - analogs & derivatives Propane - chemical synthesis Propane - chemistry Rhodium - chemistry Stereoisomerism
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	In the presence of catalytic amounts of RhH(CO)(PPh3)3 and 1,2-bis(diphenylphosphino)benzene (dppBz), acyl groups were transferred between benzyl ketones and thioesters/aryl esters. The rhodium complex catalyzed the cleavage of ketone CO–C bonds and intermolecular rearrangement giving unsymmetric ketones. The acyl-transfer reaction also occurred with 1-(p-chlorophenyl)-3-(p-cyanophenyl)propane-2-one giving unsymmetric ketones.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol3017148