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Org Lett. 2014 Jun 6;16(11):2934-7. doi: 10.1021/ol5010752. Epub 2014 May 15.

Facile synthesis of 3-aryloxindoles via brønsted acid catalyzed Friedel-Crafts alkylation of electron-rich arenes with 3-diazooxindoles.

Author information

1
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, and Department of Chemistry, East China Normal University , 3663 North Zhongshan Road, Shanghai 200062, China.

Abstract

A simple metal-free method for the synthesis of 3-aryloxindoles via Brønsted acid catalyzed aromatic C-H functionalization of electron-rich arenes with 3-diazooxindoles is developed. In the presence of a catalytic amount of TfOH, a series of 3-aryloxindoles are synthesized as single regioisomers in good to excellent yields. This transformation is proposed to proceed through acid-catalyzed protonation of 3-diazooxindoles into diazonium ions followed by Friedel-Crafts-type alkylation of arenes.

PMID:
24831829
DOI:
10.1021/ol5010752
[Indexed for MEDLINE]

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