Azo-Compound-Mediated Cyanoalkylation of Alkenes by Copper Catalysis: General Access to Cyano-Substituted Oxindoles

Shi Tang; Dong Zhou; Zhi-Hao Li; Mei-Jun Fu; Li Jie; Rui-Long Sheng; Shu-Hua Li

doi:10.1055/s-0034-1379902

Synthesis, Table of Contents

Synthesis 2015; 47(11): 1567-1580
DOI: 10.1055/s-0034-1379902

paper

Azo-Compound-Mediated Cyanoalkylation of Alkenes by Copper Catalysis: General Access to Cyano-Substituted Oxindoles

Authors

Shi Tang*

^aCollege of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, P. R. of China
Dong Zhou

^aCollege of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, P. R. of China
Zhi-Hao Li

^aCollege of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, P. R. of China

^bShanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China Email: stang@jsu.edu.cn Email: rlsheng@sioc.ac.cn
Mei-Jun Fu

^aCollege of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, P. R. of China
Li Jie

^aCollege of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, P. R. of China
Rui-Long Sheng*

^bShanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China Email: stang@jsu.edu.cn Email: rlsheng@sioc.ac.cn
Shu-Hua Li

^aCollege of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, P. R. of China

Abstract

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Abstract

A practical and highly efficient azo-compound-mediated/ promoted radical cyanoalkylation of activated alkenes by copper catalysis was developed, which allowed for general synthesis of oxindoles bearing various nitrile moieties, especially the rarely reported 3° nitrile moiety via cascade radical addition/C(sp²)–H cyclization. This protocol demonstrates that DIAD served for a new promoter instead of usual Ag salts or bases in the C(sp³)–H functionalization of acetonitrile for the first time. The use of readily available AIBN and beyond as the radical sources, and inexpensive copper as the catalyst, as well as the simplicity of operation and handling, make this protocol an attractive access to therapeutically important cyano-substituted oxindoles.

Key words

azo compounds - cyanoalkylation - alkenes - radical - copper catalysis

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References

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Supplementary Material

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