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Updated: Jan 22, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Controllable synthesis of 3-chloro- and 3,3-dichloro-2-oxindoles via hypervalent iodine-mediated chlorooxidation
Xinpeng Jiang1, Liechao Yang1, Wenlong Yang1
1College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, P.R. China. ycm@zjut.edu.cn.
Abstract:
An efficient and controllable protocol for the synthesis of 3-chloro- and 3,3-dichloro-2-oxindoles has been developed via hypervalent iodine-promoted chlorooxidation. By using two equivalents of 1-chloro-1,2-benziodoxol-3-(1H)-one, a wide range of indoles were transformed into 3-chloro-2-oxindoles in DMF/CF3CO2H/H2O at room temperature with good yields. As far as we know, this is the first report on the selective C-2 oxidation and C-3 monochlorination of simple indoles. In addition, three equivalents of the same hypervalent iodine afforded 3,3-dichloro-2-oxindoles in up to 99% yields under optimized conditions (dioxane/H2O, 80 °C). The method features mild reaction conditions, the widespread availability of the substrates, and good functional group tolerance.
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