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

The aromatization of α-tetralones substituted at the β-position by an ester group is reported using either CuI or Pd2(dba)3. In the case of using CuI (10 mol%) as catalyst and Cs2CO3 as base in dioxane, 2-(methoxycarbonyl)-α-tetralones are smoothly converted into the corresponding methyl 1-hydroxy-2...

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Bibliographic Details
Published in:Tetrahedron 2016-04, Vol.72 (16), p.1897-1902
Main Authors: Cívicos, José F., Ribeiro, Carlos M.R., Costa, Paulo R.R., Nájera, Carmen
Format: Article
Language:English
Subjects:
Argon
Catalysis
Catalysts
Copper
Economics
Esters
Naphthols
Palladium
Synthesis
Tetrahedrons
Tetralones
Toluene
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Summary:The aromatization of α-tetralones substituted at the β-position by an ester group is reported using either CuI or Pd2(dba)3. In the case of using CuI (10 mol%) as catalyst and Cs2CO3 as base in dioxane, 2-(methoxycarbonyl)-α-tetralones are smoothly converted into the corresponding methyl 1-hydroxy-2-naphthoates at 70 °C under air. Alternatively, Pd2(dba)3 (1.25 mol%) can also be used as catalyst in the presence of K3PO4 as base in toluene also at 70 °C under argon. These are the most straightforward methodologies for the aromatization of these types of α-tetralones. CuI is the catalyst of choice due to higher efficiency, economical and practical reasons. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2016.01.057