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

doi:10.6023/cjoc201410032

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

Notes

铁粉促进断裂Se—Se键及其应用于合成α-芳硒基羰基化合物

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

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 E-mail:xhx1581@hnu.edu.cn
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 Yuejun^a,b, Guo Cuixia^b, Qiu Renhua^b, Li Ningbo Chen Jinyang^b, Xu Xinxua^b

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).

1. Iron-Mediated Cleavage of Se—Se Bond for the Synthesis of α-Arylseleno Carbonyl Compounds.PDF(987KB)

Abstract

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

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Ouyang Yuejun, Guo Cuixia, Qiu Renhua, Li Ningbo Chen Jinyang, Xu Xinxua. Iron-Mediated Cleavage of Se—Se Bond for the Synthesis of α-Arylseleno Carbonyl Compounds[J]. Chin. J. Org. Chem., 2015, 35(3): 731-734.

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铁粉促进断裂Se—Se键及其应用于合成α-芳硒基羰基化合物

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

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