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Additive-free oxychlorination of unsaturated C–C bonds with <i>tert</i>-butyl hypochlorite and water

Duyi Shen, Chaoyue Sun, Yun Han, Zhen Luo, Ting Ren, Qin Zhang, Wenting Huang, Jianru Xie, Ying Jia, Mianran Chao

2024Organic & Biomolecular Chemistry11 citationsDOI

Abstract

-alkenes has been compared and rationalized. Using a group of control experiments, the possible mechanisms have been proposed as the initial electrophilic chlorination of unsaturated C-C bonds in a Markovnikov-addition manner in general followed by a nucleophilic addition with water. This work simplified the oxychlorination method with a mild chlorine source and a green oxygen source under ambient conditions.

Topics & Concepts

ChemistryReagentChlorineElectrophileNucleophileHypochloriteOxygenMarkovnikov's ruleDouble bondAllylic rearrangementOrganic chemistryArylMedicinal chemistryCatalysisRegioselectivityAlkylVanadium and Halogenation ChemistryOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization Methods