Highly efficient palladium-catalyzed Suzuki–Miyaura reactions of potassium aryltrifluoroborates with 5-iodo-1,3-dioxin-4-ones in water: an approach to α-aryl-β-ketoesters

• Published in: Tetrahedron 2010-01, Vol.66 (3), p.773-779
• Main Authors: Vieira, Adriano S., Cunha, Rodrigo L.O.R., Klitzke, Clécio F., Zukerman-Schpector, Julio, Stefani, Hélio A.
• Format: Article
• Language: English
• Subjects: Catalysis; Catalysts: preparations and properties; Chemistry; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Organic chemistry; Potassium aryltrifluoroborates; Preparations and properties; Suzuki–Miyaura; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Water; α-Aryl-β-ketoesters
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2009.11.027

The high efficient palladium-catalyzed Suzuki–Miyaura reactions of potassium aryltrifluoroborates 3 with 5-iodo-1,3-dioxin-4-ones 2a–b in water as only solvent in the presence of n-Bu4NOH as base is reported. The respective 5-aryl-1,3-dioxin-4-ones 4a–n were obtained in good to excellent yields. The catalyst system provides high efficiency at low load using electronically diverse coupling partners. The obtained 2,2,6-trimethyl-5-aryl-1,3-dioxin-4-ones were transformed into corresponding α-aryl-β-ketoesters 6 by reaction with an alcohol in the absence of solvent. [Display omitted]