Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 21, Pages 10390-10398Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo501989x
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Funding
- NSFC [21372002, 21232007]
- Open Foundation of Jiangsu Key Laboratory [K201314]
- JSNU
- PAPD of Jiangsu Province
- Cling Lan Project
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An organocatalytic arylation of 3-indolylmethanols has been established via chemo- and regiospecific C6-functionalization of 2,3-disubstituted indoles, leading to the production of bisindolyloxindoles containing an all-carbon quaternary stereocenter in high yields (up to 99% yield). This reaction not only represents the first catalytic arylation of 3-indolylmethanols using 2,3-disubstituted indoles as aromatic nucleophiles but also serves as a good example of direct catalytic C6-functionalization of indoles, which have been scarcely investigated. Besides, this approach also provides an efficient method to access a biologically important 3,3'-disubstituted oxindole framework and a 3',6-linked bisindole skeleton. Furthermore, the investigation of the activation mode suggested that the dual activation of an ion pair and H-bond between the substrates and the catalyst cooperatively contributed to the success of the reaction.
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