Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (3): 731-734.DOI: 10.6023/cjoc201410032 Previous Articles     Next Articles



欧阳跃军a,b, 郭翠霞b, 邱仁华b, 李宁波b, 陈锦杨b, 许新华b   

  1. a 湖南怀化学院 怀化 428000;
    b 湖南大学化学化工学院 长沙 410082
  • 收稿日期:2014-10-23 修回日期:2014-11-12 发布日期:2014-11-28
  • 通讯作者: 邱仁华, 许新华
  • 基金资助:

    国家自然科学基金(No. 21273068)、湖南省科技计划(No. 2013FJ3023)资助项目.

Iron-Mediated Cleavage of Se—Se Bond for the Synthesis of α-Arylseleno Carbonyl Compounds

Ouyang Yuejuna,b, Guo Cuixiab, Qiu Renhuab, Li Ningbo Chen Jinyangb, Xu Xinxuab   

  1. a Department of Chemistry and Chemical Engineering, Huaihua University, Huaihua 418000;
    b College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082
  • Received:2014-10-23 Revised:2014-11-12 Published:2014-11-28
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21273068), the Planned Science and Technology Project of Hunan Province (No. 2013FJ3023).

In the presence of iron dust, using commercial N,N-dimethylformamide (DMF) as solvent, diaryl diselenides reacted with α-bromo carbonyl compounds at 90 ℃ under nitrogen atmosphere to afford a series of α-arylseleno carbonyl compounds. The influence of temperature, reaction time, solvent and iron dosage on the reaction was investigated. The results showed that the influence of temperature on the reaction was most obvious. In addition, the influence of carbonyl substituent in α-bromo carbonyl compounds was also more obvious. When carbonyl substituent is phenyl, the yield was lower than that of methyl or alkoxy. A proposal mechanism is that iron dust reacted with diaryl diselenides to give the nucleophilic species ArSeFeSeAr, and nucleophilic species ArSeFeSeAr and electrophilic α-bromo carbonyl compounds occured nucleophilic substitution reaction to obtain the desire products. The method using the iron dust to promote the cleavage of Se—Se bond has advantages of safe non-toxic, cheap and easy to get raw materials, simple procedure.

Key words: iron dust, cleavage of Se—Se bond, diaryl diselenides, α-bromo carbonyl compounds, α-arylseleno carbonyl compounds