K3PO4-Catalyzed Regiospecific Bromoamidation of β, β-Dicyanostyrene Derivatives with N-Bromoacetamide(NBA)

doi:10.1007/s40242-014-3234-8

Chemical Research in Chinese Universities ›› 2014, Vol. 30 ›› Issue (2): 266-271.doi: 10.1007/s40242-014-3234-8

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K₃PO₄-Catalyzed Regiospecific Bromoamidation of β, β-Dicyanostyrene Derivatives with N-Bromoacetamide(NBA)

CHEN Zhanguo^1,2, LI Yanan^1,2, ZHOU Jimei^1,2, WANG Dan^1,2, GE Miao³

1. Key Laboratory for Macromolecular Science of Shaanxi Province, Xi'an 710119, P. R. China;
2. School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, P. R. China;
3. Tourism and Environment College of Shaanxi Normal University, Xi'an 710119, P. R. China

Received:2013-05-27 Revised:2013-08-19 Online:2014-04-01 Published:2013-09-24
Contact: CHEN Zhanguo E-mail:chzhg@snnu.edu.cn
Supported by:
Supported by the Natural Science Foundation of Shaanxi Province, China(No.2009JM2001), the Innovation Foundation of Pastgraduate Cultivation of Shaanxi Normal University, China(No.2008CXB009) and Fundamental Research Funds for the Central Universities of China(No.GK261001095).

Abstract

Abstract:

An efficient method for the bromoamidation of β,β-dicyanostyrene derivatives with N-bromoacetamide (NBA) was developed. This protocol provides a convenient process to convert β,β-dicyanostyrene derivatives into the vicinal haloamines in excellent yields(up to 99%) at room temperature in the presence of anhydrous K₃PO₄as a catalyst without the protection of the inert gaseous in CH₂Cl₂. A total of 11 examples were investigated and all the products showed the regionspecific feature. Based on the observation of different activities for the different substrates involving the electron-rich or electron-deficient β,β-dicyanostyrenes, a possible Michael addition mechanism was proposed.

Key words: Bromoamidation, β,β-Dicyanostyrene derivative, N-Bromoacetamide, Regiospecificity, Catalytic reaction

CHEN Zhanguo, LI Yanan, ZHOU Jimei, WANG Dan, GE Miao. K₃PO₄-Catalyzed Regiospecific Bromoamidation of β, β-Dicyanostyrene Derivatives with N-Bromoacetamide(NBA)[J]. Chemical Research in Chinese Universities, 2014, 30(2): 266-271.

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K₃PO₄-Catalyzed Regiospecific Bromoamidation of β, β-Dicyanostyrene Derivatives with N-Bromoacetamide(NBA)

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