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Organic & biomolecular chemistry

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


PMID 22499237

Abstract

Cu(I)-catalyzed reaction of o-bromobenzaldehydes with β-ketoesters using Cs(2)CO(3) 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.