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Issue 28, 2019
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Controllable synthesis of 3-chloro- and 3,3-dichloro-2-oxindoles via hypervalent iodine-mediated chlorooxidation

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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.

Graphical abstract: Controllable synthesis of 3-chloro- and 3,3-dichloro-2-oxindoles via hypervalent iodine-mediated chlorooxidation

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Article information


Submitted
19 May 2019
Accepted
28 Jun 2019
First published
29 Jun 2019

Org. Biomol. Chem., 2019,17, 6920-6924
Article type
Paper

Controllable synthesis of 3-chloro- and 3,3-dichloro-2-oxindoles via hypervalent iodine-mediated chlorooxidation

X. Jiang, L. Yang, W. Yang, Y. Zhu, L. Fang and C. Yu, Org. Biomol. Chem., 2019, 17, 6920
DOI: 10.1039/C9OB01173K

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