Issue 22, 2024

Catalyst- and base-free visible light-enabled radical relay trihalomethylation/functional group-migration/carbonylation with CX3SO2Cl

Abstract

Herein, we report a visible light-enabled radical trihalomethylation/cyano-migration/carbonylation cascade reaction of 2-hydroxy-2-hex-5-enenitrile with CX3SO2Cl as the CX3-source (X = F, Cl) to obtain 5-oxo-2-(2,2,2-trihaloethyl)pentanenitrile compounds in the absence of a photocatalyst, transition metal and base. This reaction system is also effective to convert (benzo[d]thiazol-2-yl)-pent-4-enol to the corresponding 4-(benzo[d]thiazol-2-yl)-6,6,6-trihalo-hexanone products. These reactions occur under mild conditions, tolerate a wide range of functional groups, and provide alternative approaches for the 1,2-bifunctionalization reaction of unactivated olefins.

Graphical abstract: Catalyst- and base-free visible light-enabled radical relay trihalomethylation/functional group-migration/carbonylation with CX3SO2Cl

Supplementary files

Article information

Article type
Paper
Submitted
23 Feb 2024
Accepted
05 Apr 2024
First published
16 Apr 2024

Org. Biomol. Chem., 2024,22, 4488-4493

Catalyst- and base-free visible light-enabled radical relay trihalomethylation/functional group-migration/carbonylation with CX3SO2Cl

J. Hu, C. Yang, X. Qin, H. Liu, T. Ma, A. Shi, Q. Lv, X. Liu, J. Yang and D. Li, Org. Biomol. Chem., 2024, 22, 4488 DOI: 10.1039/D4OB00292J

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