Issue 41, 2023

Regioselective [2 + 1] photocycloaddition of 2-pyridones with diazo compounds

Abstract

Herein, we report a novel regioselective [2 + 1] cyclization reaction of 2-pyridones with carbenes generated in situ via visible light irradiation, without the requirement for catalysts or additives. The diverse functional groups of 2-pyridones and diazo compounds exhibit good tolerance, enabling the rapid synthesis of highly valuable cyclopropanated dihydro-2-pyridone scaffolds with exceptional regio- and stereoselectivity. Furthermore, DFT calculations provide a comprehensive explanation for the regio- and stereoselectivity observed in the reaction.

Graphical abstract: Regioselective [2 + 1] photocycloaddition of 2-pyridones with diazo compounds

Supplementary files

Article information

Article type
Communication
Submitted
23 Aug 2023
Accepted
02 Oct 2023
First published
03 Oct 2023

Org. Biomol. Chem., 2023,21, 8273-8278

Regioselective [2 + 1] photocycloaddition of 2-pyridones with diazo compounds

F. He, Z. Sun, C. Li, Z. Jiang, H. Miao, Q. Li and C. Wu, Org. Biomol. Chem., 2023, 21, 8273 DOI: 10.1039/D3OB01354E

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