Fe-promoted radical cyanomethylation/arylation of arylacrylamides to access oxindoles via cleavage of the sp(3) C-H of acetonitrile and the sp(2) C-H of the phenyl group

Changduo Pan; Honglin Zhang; Chengjian Zhu

doi:10.1039/c4ob02172j

Fe-promoted radical cyanomethylation/arylation of arylacrylamides to access oxindoles via cleavage of the sp(3) C-H of acetonitrile and the sp(2) C-H of the phenyl group

Org Biomol Chem. 2015 Jan 14;13(2):361-4. doi: 10.1039/c4ob02172j.

Authors

Changduo Pan¹, Honglin Zhang, Chengjian Zhu

Affiliation

¹ State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. China. cjzhu@nju.edu.cn.

PMID: 25388144
DOI: 10.1039/c4ob02172j

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 sp(3) C-H of acetonitrile and the sp(2) 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.