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Type: Artigo de periódico
Title: Palladium-Catalyzed Tandem Heck-Lactonization from o-Iodophenols and Enoates: Synthesis of Coumarins and the Study of the Mechanism by Electrospray Ionization Mass Spectrometry
Author: Fernandes, TD
Vaz, BG
Eberlin, MN
da Silva, AJM
Costa, PRR
Abstract: The tandem Heck-lactonization reaction between enoates Z-1a,b, E-1a, E-2a-d, Z-2e, 2f, and o-iodophenols (4a-f) was studied in the presence of substoichiometric amounts of Pd(OAc)(2) or PdCl(2), under experimental conditions favoring the cationic mechanism (conditions A, B, and C), leading to coumarins 5a-f and 6a-e. Moderate to excellent yields were obtained under aqueous conditions (conditions A and B). Using electrospray ionization for transferring ions directly from solution to the gas phase, and mass spectrometry for structural assignments, key cationic palladium intermediates have been successfully intercepted and structurally characterized for the first time for this type of reaction.
Country: EUA
Editor: Amer Chemical Soc
Citation: Journal Of Organic Chemistry. Amer Chemical Soc, v. 75, n. 21, n. 7085, n. 7091, 2010.
Rights: fechado
Identifier DOI: 10.1021/jo1010922
Date Issue: 2010
Appears in Collections:Unicamp - Artigos e Outros Documentos

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