Regiospecific ortho‐C−H Allylation of Benzoic Acids. (5th March 2018)

• Record Type: Journal Article
• Authors: Trita, A. Stefania; Biafora, Agostino; Pichette Drapeau, Martin; Weber, Philip; Gooßen, Lukas J.
• Is Part Of: Angewandte Chemie. Volume 130:Number 44(2018)
• Page Start: 14788
• Page End: 14792
• Publication Date: 2018-03-05
• Subjects: Allylierungen -- C-H-Aktivierung -- Carbonsäuren -- Reaktionsmechanismen -- Ruthenium; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201712520
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: A carboxylate‐directed ortho ‐C−H functionalization has been developed and it allows the regiospecific introduction of allyl residues to benzoic acids. In the presence of a [Ru( p ‐cymene)Cl2 ]2 and K3 PO4, benzoic acids react with allyl acetates at only 50 °C to give the corresponding ortho ‐allylbenzoic acids. The protocol is generally applicable to both electron‐rich and electron‐poor benzoic acids in combination with linear and branched allyl acetates. The products can be further functionalized in situ, for example, by double‐bond migration, lactonization, or decarboxylation.