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Synthesis 2011(22): 3680-3686  
DOI: 10.1055/s-0030-1260245
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Potassium Carbonate Catalyzed Regioselective Aminohalogenation of β-Nitrostyrenes by Using Benzyl Carbamate/N-Chlorosuccinimide as a New Nitrogen/Chlorine Source

Xiaoyun Jia, Haibo Meia, Yu Qiana, Jianlin Han*a, Guigen Lia,c, Yi Pan*a,b
a School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China
Fax: +86(25)83593153 ; e-Mail: hanjl@nju.edu.cn; Fax: +86(25)83592846; e-Mail: yipan@nju.edu.cn;
b State Key Lab of Coordination Chemistry, Nanjing University, Nanjing 210093, P. R. of China
c Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA
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Publication History

Received 29 July 2011
Publication Date:
29 September 2011 (online)

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Abstract

A combination of benzyl carbamate and N-chlorosuccinimide was developed as a new system for aminohalogenation of β-nitrostyrenes catalyzed by potassium carbonate in dichloromethane at room temperature. The reaction tolerates a wide range of substituents on the β-nitrostyrene, and proceeds smoothly in good-to-excellent­ chemical yields (77-99%). The new system shows a high efficiency and it markedly shortens the reaction time for aminochlorination. N,N-Dichlorobenzyl carbamate was also found to be a highly efficient source of both nitrogen and chlorine for the aminohalogenation reaction.

Key words

aminations - chlorinations - alkenes - carbamates - amides

    Primary data for this article are available online and can be cited using the following DOI: 10.4125/pd0019th:
  • Primary Data

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