Copper- versus palladium-catalyzed aromatization of 2-(methoxycarbonyl) tetralones: synthesis of methyl 1-hydroxy-2-naphthoates

TETRAHEDRON

卷:72

Article

Civicos, Jose F.³  Ribeiro, Carlos M. R.^1,2,4  Costa, Paulo R. R.³  Najera, Carmen^1,2 

[1] Univ Alicante, Fac Sci, Dept Organ Chem, E-03080 Alicante, Spain

[2] Univ Alicante, Fac Sci, Ctr Innovac Quim Avanzada ORFEO CINQA, E-03080 Alicante, Spain

[3] Univ Fed Rio de Janeiro, Ctr Ciencias Saude, Nucleo Pesquisas Prod Nat, Bloco H,Ilha Cidade Univ, BR-21941590 Rio De Janeiro, RJ, Brazil

[4] Univ Fed Fluminense, Dept Quim Organ, Inst Quim, Outeiro Sao Joao Batista S-N, BR-24020141 Rio De Janeiro, Brazil

关键词: Tetralones;    Naphthols;    Copper;    Palladium;    Catalysis;   

DOI  :  10.1016/j.tet.2016.01.057

来源: Elsevier

【 摘 要 】

The aromatization of alpha-tetralones substituted at the beta-position by an ester group is reported using either CuI or Pd-2(dba)(3). In the case of using CuI (10 mol%) as catalyst and Cs2CO3 as base in dioxane, 2-(methoxycarbonyl)-alpha-tetralones are smoothly converted into the corresponding methyl 1-hydroxy-2-naphthoates at 70 degrees C under air. Alternatively, Pd-2(dba)(3) (1.25 mol%) can also be used as catalyst in the presence of K3PO4 as base in toluene also at 70 degrees C under argon. These are the most straightforward methodologies for the aromatization of these types of alpha-tetralones. CuI is the catalyst of choice due to higher efficiency, economical and practical reasons. (C) 2016 Elsevier Ltd. All rights reserved.

【 授权许可】

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