Hydroselenation of Terminal Alkynes Catalyzed by Cesium Hydroxide: Highly Stereo- and Regio-selective Synthesis of (E)-1-Arylselenoalkenes

doi:10.6023/cjoc201211028

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (03): 558-561.DOI: 10.6023/cjoc201211028 Previous Articles Next Articles

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氢氧化铯催化端炔氢硒化: 高立体区域选择性合成(E)-1-芳硒基烯烃

王小勇^a, 李治章^a, 张卫军^a, 王勰^b, 陈锦杨^b, 李宁波^b, 邱仁华^b, 许新华^b

a 湖南科技学院生命科学与化工系永州 425100;
b 湖南大学化学化工学院长沙 410082

收稿日期:2012-11-15 修回日期:2012-12-11 发布日期:2012-12-13
通讯作者: 李治章, 许新华 E-mail:xhx1581@yahoo.com.cn
基金资助:
湖南省自然科学基金(No. 11JJ2009)和国家自然科学基金(No. 21273068)资助项目.

Hydroselenation of Terminal Alkynes Catalyzed by Cesium Hydroxide: Highly Stereo- and Regio-selective Synthesis of (E)-1-Arylselenoalkenes

Wang Xiaoyong^a, Li Zhizhang^a, Zhang Weijun^a, Wang Xie^b, Chen Jinyang^b, Li Ningbo^b, Qiu Renhua^b, Xu Xinhua^b

a Department of Life Science and Chemical Engineering, Hunan University of Science and Engineering, Yongzhou 425100;
b College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received:2012-11-15 Revised:2012-12-11 Published:2012-12-13
Supported by:
Project supported by the Natural Science Foundation of Hunan Province (No. 11JJ2009) and the National Natural Science Foundation of China (No. 21273068).

In the presence of catalytic amount of cesium hydroxide, the hydroselenation of terminal alkynes occurred in N,N-dimethylformamide (DMF) at room temperature under nitrogen atmosphere to afford (E)-1-organseleno-1-alkene in high yields. The reaction mechanism is that selenols reacted with cesium hydroxide to give cesium selenides, which underwent nucleophilic addition to the alkynes to form selenium vinylic anion, hydrolyzed to give product (E)-1-organoselenovinylene and catalyst cesium hydroxide. The method could provide a new and expedient way for the hydroselenation of unactivated alkynes.

Key words: nucleophilic addition, regioselectivity, terminal alkyne, hydroselenolation, cesium hydroxide, (E)-1-organoseleno-1-alkene

Cite this article

Wang Xiaoyong, Li Zhizhang, Zhang Weijun, Wang Xie, Chen Jinyang, Li Ningbo, Qiu Renhua, Xu Xinhua. Hydroselenation of Terminal Alkynes Catalyzed by Cesium Hydroxide: Highly Stereo- and Regio-selective Synthesis of (E)-1-Arylselenoalkenes[J]. Chin. J. Org. Chem., 2013, 33(03): 558-561.

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氢氧化铯催化端炔氢硒化: 高立体区域选择性合成(E)-1-芳硒基烯烃

Hydroselenation of Terminal Alkynes Catalyzed by Cesium Hydroxide: Highly Stereo- and Regio-selective Synthesis of (E)-1-Arylselenoalkenes

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