Issue 16, 2023

Photocatalytic synthesis of azaheterocycle-fused piperidines and pyrrolidines via tandem difunctionalization of unactivated alkenes

Abstract

A variety of azaheterocycle-fused piperidines and pyrrolidines bearing CF3 and CHF2 functionalities were obtained using CF3SO2Na and CHF2SO2Na by visible light photocatalysis. This protocol involves a radical cascade cyclization via tandem tri- and difluoromethylation–arylation of pendent unactivated alkenes. Benzimidazole, imidazole, theophylline, purine, and indole serve as applicable anchors, thereby enriching the structural diversity of piperidine and pyrrolidine derivatives. This method features mild, additive-free and transition metal-free conditions.

Graphical abstract: Photocatalytic synthesis of azaheterocycle-fused piperidines and pyrrolidines via tandem difunctionalization of unactivated alkenes

Supplementary files

Article information

Article type
Communication
Submitted
15 Feb 2023
Accepted
28 Mar 2023
First published
28 Mar 2023

Org. Biomol. Chem., 2023,21, 3317-3322

Photocatalytic synthesis of azaheterocycle-fused piperidines and pyrrolidines via tandem difunctionalization of unactivated alkenes

Q. Zhou, J. Dai, W. Zhao, X. Zhong, C. Liu, W. Luo, Z. Li, J. Li and W. Liu, Org. Biomol. Chem., 2023, 21, 3317 DOI: 10.1039/D3OB00241A

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