Issue 38, 2023

A facile synthesis of phthalimides from o-phthalaldehyde and amines via tandem cyclocondensation and α-C–H oxidation by an electrochemical oxygen reduction reaction

Abstract

Electrochemical synthesis of phthalimides from o-phthalaldehyde and amines via tandem cyclocondensation and α-C–H oxygenation of isoindolinone was achieved. The α-C–H oxidation proceeded with molecular oxygen via an oxygen reduction reaction (ORR) on the cathode under electrochemical conditions. The synthetic utility of this protocol was successfully demonstrated by employing gram-scale synthesis and obtaining bioactive molecules such as thalidomide and 2-(2,6-diisopropylphenyl)-5-hydroxyisoindoline-1,3-dione. Mechanistic studies and control experiments indicate that molecular oxygen provides oxygen atoms for the reaction.

Graphical abstract: A facile synthesis of phthalimides from o-phthalaldehyde and amines via tandem cyclocondensation and α-C–H oxidation by an electrochemical oxygen reduction reaction

Supplementary files

Article information

Article type
Communication
Submitted
28 Jun 2023
Accepted
05 Sep 2023
First published
05 Sep 2023

Org. Biomol. Chem., 2023,21, 7707-7711

A facile synthesis of phthalimides from o-phthalaldehyde and amines via tandem cyclocondensation and α-C–H oxidation by an electrochemical oxygen reduction reaction

N. Neerathilingam, S. Prabhu and R. Anandhan, Org. Biomol. Chem., 2023, 21, 7707 DOI: 10.1039/D3OB01031G

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