Issue 2, 2015

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

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

Supplementary files

Article information

Article type
Communication
Submitted
11 Oct 2014
Accepted
30 Oct 2014
First published
30 Oct 2014

Org. Biomol. Chem., 2015,13, 361-364

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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