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Issue 2, 2015
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Fe-promoted radical cyanomethylation/arylation of arylacrylamides to access oxindoles via cleavage of the sp3 C–H of acetonitrile and the sp2 C–H of the phenyl group

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Abstract

Radical cyanomethylation/arylation of arylacrylamides to access oxindoles with acetonitrile as the radical precursor is described. This reaction involves dual C–H bond functionalization, including the sp3 C–H of acetonitrile and the sp2 C–H of the phenyl group. A variety of functional groups, such as methoxy, ethyloxy carbonyl, chloro, bromo, iodo, nitro, trifluoromethoxy and trifluoromethyl groups, are well tolerated.

Graphical abstract: Fe-promoted radical cyanomethylation/arylation of arylacrylamides to access oxindoles via cleavage of the sp3 C–H of acetonitrile and the sp2 C–H of the phenyl group

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Article information


Submitted
11 Oct 2014
Accepted
30 Oct 2014
First published
30 Oct 2014

Org. Biomol. Chem., 2015,13, 361-364
Article type
Communication

Fe-promoted radical cyanomethylation/arylation of arylacrylamides to access oxindoles via cleavage of the sp3 C–H of acetonitrile and the sp2 C–H of the phenyl group

C. Pan, H. Zhang and C. Zhu, Org. Biomol. Chem., 2015, 13, 361
DOI: 10.1039/C4OB02172J

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