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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 Synthesis Of Flavonoids
Author: Machado A.H.L.
de Sousa M.A.
Patto D.C.S.
Azevedo L.F.S.
Bombonato F.I.
Correia C.R.D.
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 4NHSO 4 as additive or 4-NO 2PhN 2BF 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. © 2009 Elsevier Ltd. All rights reserved.
Rights: fechado
Identifier DOI: 10.1016/j.tetlet.2009.01.017
Date Issue: 2009
Appears in Collections:Unicamp - Artigos e Outros Documentos

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