Metal-free direct cyanoisopropylation/arylation of N-arylacrylamides or N-alkyl-N-(arylsulfonyl)acrylamid es with AIBN: a simple and mild approach to cyano-containing oxindoles

A simple and metal-free direct cyanoisopropylation/arylation of N-arylacrylamides or N-alkyl-N-(arylsulfonyl)acrylamid es with AIBN has been developed with cheap and readily available CH sub(3)NO sub(2) as both the solvent and the oxidant. This reaction provides an efficient approach to cyano-contai...

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Bibliographic Details
Published in:RSC advances 2015-06, Vol.5 (70), p.56438-56443
Main Authors: Zhang, Mingzhong, Sheng, Wenbing, Ji, Pengyi, Liu, Yufeng, Guo, Cancheng
Format: Article
Language:English
Subjects:
Aromatic compounds
Bonding
Catalysis
Handles
Migration
Oxidants
Oxidizing agents
Solvents
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Summary:A simple and metal-free direct cyanoisopropylation/arylation of N-arylacrylamides or N-alkyl-N-(arylsulfonyl)acrylamid es with AIBN has been developed with cheap and readily available CH sub(3)NO sub(2) as both the solvent and the oxidant. This reaction provides an efficient approach to cyano-containing oxindoles, which are highly valued synthetic intermediates of biologically active molecules. A series of N-alkyl-N-(arylsulfonyl)acrylamid e substrates could be converted into the corresponding oxindoles in good yields and with excellent chemoselectivity viaone-pot cyanoisopropylation/aryl migration/desulfonylation and C(sp super(2))-N bond formation. In contrast to previous reports, the mild conditions together with lack of a need for any metal catalysts and additional oxidants make this protocol very easy to handle and practical.
ISSN:2046-2069
DOI:10.1039/c5ra10084d