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

Publikations-Art

Zeitschriftenbeitrag (peer-reviewed)

Autoren

Malakar, C. C; Sudheendran, K.; Imrich, H.-G.; Mika, S.; Beifuss U.

Erscheinungsjahr

2012

Veröffentlicht in

Biomol. Chem.

Band/Volume

10/

DOI

10.1039/C2OB06963F

Seite (von - bis)

3899-3905

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.