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

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 alpha-aryl-beta-ketoesters 6 by reaction with an alcohol in the absence of solvent. (C) 2009 Elsevier B.V. All rights reserved.Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Univ São Paulo, Fac Ciencias Farmaceut, BR-05508900 São Paulo, BrazilUniv Fed ABC, Ctr Ciencias Nat & Humanas, BR-5001 Santo Andre, SP, BrazilInst Butantan, Ctr Toxinol Aplicada CAT CEPID, Lab Espectrometria Massas, São Paulo, BrazilUniversidade Federal de São Paulo, Dept Quim, Sao Carlos, SP, BrazilUniversidade Federal de São Paulo, Dept Quim, Sao Carlos, SP, BrazilCNPq: CNPq 300.613/2007-5FAPESP: 06/50190-7FAPESP: 07/02382-7FAPESP: 07/59404-2Web of Scienc