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

Publication Type: Journal contribution (peer reviewed)
Authors: Malakar, C. C; Sudheendran, K.; Imrich, H.-G.; Mika, S.; Beifuss U.
Year of publication: 2012
Published in: Biomol. Chem.
Band/Volume: 10/
DOI: 10.1039/C2OB06963F
Page (from - to): 3899-3905

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.

Involved persons

Sabine Mika
Prof. Dr. rer. nat. Uwe Beifuß

Involved institutions

Institute of Chemistry
Bioorganic Chemistry