Palladium‐Catalyzed C(sp2)−H Alkylation of Aldehyde‐Derived Hydrazones with Functionalized Difluoromethyl Bromides. (16th December 2015)

• Record Type: Journal Article
• Authors: Prieto, Alexis; Melot, Romain; Bouyssi, Didier; Monteiro, Nuno
• Is Part Of: Angewandte Chemie. Volume 128:Number 5(2016)
• Page Start: 1917
• Page End: 1921
• Publication Date: 2015-12-16
• Subjects: Fluor -- Homogene Katalyse -- Hydrazone -- Palladium -- Reaktionsmechanismen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201510334
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: A palladium‐catalyzed C(sp 2 )−H difluoromethylation of aldehyde‐derived hydrazones using bromodifluoromethylated compounds to afford the corresponding functionalized difluoromethylketone hydrazones has been established. It is proposed that a radical/SET mechanism proceeding via a difluoroalkyl radical may be involved in the catalytic cycle. Applications of the methodology to the synthesis of α, α‐difluoro‐β‐ketoesters and α, α‐difluoroketones (RCOCF2 H) have been illustrated.