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

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 i...

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Published inOrganic & biomolecular chemistry Vol. 17; no. 28; pp. 6920 - 6924
Main Authors Jiang, Xinpeng, Yang, Liechao, Yang, Wenlong, Zhu, Yu, Fang, Liyun, Yu, Chuanming
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 17.07.2019
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Organic
Equivalence
Functional groups
Indoles
Iodine
Oxidation
Physical Sciences
Science & Technology
Substrates
Synthesis
DECARBOXYLATIVE HALOGENATION
OXINDOLES
INDOLECARBOXYLIC ACIDS
RECEPTOR
KINASE INHIBITORS
INDOLES
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Summary: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 degrees C). The method features mild reaction conditions, the widespread availability of the substrates, and good functional group tolerance.
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ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob01173k