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Issue 19, 2012
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Cu(I)-catalyzed annulation for the synthesis of substituted naphthalenes using o-bromobenzaldehydes and β-ketoesters as substrates

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Abstract

Cu(I)-catalyzed reaction of o-bromobenzaldehydes with β-ketoesters using Cs2CO3 as a base and 2-picolinic acid as an additive proceeds under mild conditions and gives access to substituted naphthalenes in a single step with yields ranging from 71 to 86%. The new annulation process relies on a domino Knoevenagel condensation/C-arylation/1,2-addition/carboxylic acid cleavage. The annulation can also be achieved with o-iodobenzaldehyde.

Graphical abstract: Cu(i)-catalyzed annulation for the synthesis of substituted naphthalenes using o-bromobenzaldehydes and β-ketoesters as substrates

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Publication details

The article was received on 22 Nov 2011, accepted on 09 Mar 2012 and first published on 12 Apr 2012


Article type: Paper
DOI: 10.1039/C2OB06963F
Citation: Org. Biomol. Chem., 2012,10, 3899-3905
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    Cu(I)-catalyzed annulation for the synthesis of substituted naphthalenes using o-bromobenzaldehydes and β-ketoesters as substrates

    C. C. Malakar, K. Sudheendran, H. Imrich, S. Mika and U. Beifuss, Org. Biomol. Chem., 2012, 10, 3899
    DOI: 10.1039/C2OB06963F

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