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

Jinkai Hu; Chenglei Yang; Xiaotao Qin; Hui Liu; Tongtong Ma; Ao-tong Shi; Qing-Long Lv; Xingman Liu; Jinhui Yang; Dianjun Li

doi:10.1039/D4OB00292J

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

Jinkai Hu,

^a Chenglei Yang,^a Xiaotao Qin,^a Hui Liu,^a Tongtong Ma,^a Ao-tong Shi,^a Qing-Long Lv,^a Xingman Liu,*^a Jinhui Yang*^a and Dianjun Li*^a

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* Corresponding authors

^a State Key Laboratory of High-Efficiency Utilization of Coal and Green Chemical Engineering, College of Chemistry and Chemical Engineering, Analysis and Testing Center, Ningxia University, China
E-mail: lidj2017@nxu.edu.cn, yang_jh@nxu.edu.cn

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.

Organic & Biomolecular Chemistry

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

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

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Organic & Biomolecular Chemistry