Palladium‐Catalyzed Annulation of Acyl Fluorides with Norbornene via Decarbonylation and CO Reinsertion. Issue 57 (7th September 2020)

• Record Type: Journal Article
• Authors: Sakurai, Yuka; Ogiwara, Yohei; Sakai, Norio
• Is Part Of: Chemistry. Volume 26:Issue 57(2020)
• Page Start: 12972
• Page End: 12977
• Publication Date: 2020-09-07
• Subjects: acyl fluoride -- annulation -- C−H bond cleavage -- norbornene -- palladium; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202001374
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A palladium‐catalyzed annulation of acyl fluorides with norbornene is described. This study reports the first example of an annulation of acyl fluorides in the presence of a transition‐metal catalyst. Polycyclic ketones are obtained from the cleavage of the C−F and C−H bonds of the acyl fluoride and the rearrangement of the carbonyl moiety by decarbonylation and CO reinsertion. Abstract : A Pd‐catalyzed annulation of acyl fluorides with norbornene via C−F and ortho C−H bond cleavage has been developed. The reaction proceeds via the rearrangement of CO and provides the corresponding polycyclic ketones in good to excellent yield.