An Oxidative Strategy for Generating Trichloromethyl Radical from Carbon Tetrahalides: Transition-Metal-Free Synthesis of Trichloromethylated Oxindoles

doi:10.6023/cjoc202508011

Abstract

A novel oxidative protocol for the generation of trichloromethyl radical from the cleavage of C-X bond of carbon tetrahalides has been reported. This reaction employs the combination of potassium persulfate (K₂S₂O₈) and quaternary ammonium salt (QAS) as a radical triggered system, thereby enabling the transition-metal- and organic-peroxide-free synthesis of trichloromethylated oxindoles through cascade cyclization of alkenes. The protocol delivers both high to excellent yields and good functional group tolerance. Additionally, the combination can be applied to the synthesis of α-bromoketones from ketones via the oxidative cleavage of C(sp³)-H bonds.

Key words: Radicals, Cyclization, Oxidation, Transition-metal-free

Cite this article

Zhou Ke, Wang Ze-Yong, Li Ya-Lin, Zhang Qian, Li Xin-Yue, Zou Han-Fang, Zhang Ming-Zhong, Guo Sheng-Rong, Chen Tieqiao. An Oxidative Strategy for Generating Trichloromethyl Radical from Carbon Tetrahalides: Transition-Metal-Free Synthesis of Trichloromethylated Oxindoles[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202508011.

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