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

Add time:07/12/2019    Source:sciencedirect.com

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.

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