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Type: Artigo de periódico
Title: The scope of the Heck arylation of enol ethers with arenediazonium salts: a new approach to the syntheses of flavonoids
Author: Machado, AHL
de Sousa, MA
Patto, DCS
Azevedo, LFS
Bombonato, FI
Correia, CRD
Abstract: The scope of the Heck arylation of cyclic and acyclic enol ethers with arenediazonium salts was evaluated. Arylation of 2,3-dihydrofuran yielded 2-aryl-2,5-dihydrofurans as the major adducts (>99:1) except when using n-Bu(4)NHSO(4) as additive or 4-NO(2)PhN(2)BF(4) as arenediazonium salt. 2,3-Dihydropyran provided mixtures of the three possible isomeric Heck adducts. Arylation of n-butylvinylether with arenediazonium bearing electron-donating groups resulted in substituted acetophenones as almost exclusive products in good overall yields, Substituted 4H-chromenes provided 2-aryl-2H-chromenes in moderate yield when applying the Pd(OAc)(2)/2,6-di-t-butyl-4-methylpyridine catalytic system, which were applied in the synthesis of flavonoids. (C) 2009 Elsevier Ltd. All rights reserved.
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Rights: fechado
Identifier DOI: 10.1016/j.tetlet.2009.01.017
Date Issue: 2009
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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