Copper-catalyzed Cyanoalkylation of Alkenes to Form Cyano-containing Oxindoles

doi:10.11944/j.issn.1000-0518.2015.08.150005

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (8): 884-891.DOI: 10.11944/j.issn.1000-0518.2015.08.150005

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Copper-catalyzed Cyanoalkylation of Alkenes to Form Cyano-containing Oxindoles

LI Zhihao^a,TANG Shi^a^b^*(),ZHOU Dong^a,DENG Youlin^a,LI Yuhua^a,LI Shuhua^a

^a Key Laboratory of Hu'nan Forest Product and Chemical Industry Engineering, Jishou University, Zhangjiajie, Hu'nan 416000, China
^b College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China

Received:2015-01-06 Accepted:2015-05-06 Published:2015-08-08 Online:2015-08-08
Contact: TANG Shi
Supported by:
Supported by the National Natural Science Foundation of China(NSFC)(No.21462017 ), Key Laboratory of Hunan Forest Product and Chemical Industry Engineering(No;JDZ201402), Research-Based Learning and Innovative Experiment Project of Jishou University

Abstract

Abstract:

A practical, mild and highly efficient cyanoalkylation reaction of activated alkenes by copper catalysis has been developed. In the presence of CuI/DTBP(Di-tert-butyl peroxide), N-arylacrylamide undergoes radical cyclization smoothly, and affords a series of pharmaceutically important oxindoles bearing an α-cyano quaternary carbon center. The protocol features broad substrate scope, simplicity of operation and handling, and inexpensive catalytic systems. In addition, the synthetic application and possible mechanism process in the cyclization reaction were also demonstrated.

Key words: polymer microgel, α-cyano azo compounds, cyano-containing oxindoles, C—H cyclization, radical, copper catalysis

CLC Number:

LI Zhihao, TANG Shi, ZHOU Dong, DENG Youlin, LI Yuhua, LI Shuhua. Copper-catalyzed Cyanoalkylation of Alkenes to Form Cyano-containing Oxindoles[J]. Chinese Journal of Applied Chemistry, 2015, 32(8): 884-891.

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Copper-catalyzed Cyanoalkylation of Alkenes to Form Cyano-containing Oxindoles

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