Efficient Synthesis of Unsymmetrical Selenides Promoted by Titanocene Perfluorobutanesulfonate/Zinc Catalytic System

doi:10.6023/cjoc201812033

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (6): 1802-1807.DOI: 10.6023/cjoc201812033 Previous Articles Next Articles

Notes

茂钛全氟丁基磺酸盐/锌粉体系高效催化不对称单硒醚合成

王灵晓^a, 李宁波^a, 王浩江^a, 刘文^a, 刁海鹏^a, 许新华^b

a 山西医科大学基础医学院太原 030001;
b 湖南大学化学化工学院长沙 410082

收稿日期:2018-12-19 修回日期:2019-02-03 发布日期:2019-02-22
通讯作者: 李宁波, 刁海鹏 E-mail:ningboli@sxmu.edu.cn;diaohp@sxmu.edu.cn
基金资助:
国家自然科学基金（No.21802093）、山西省青年科学基金（No.201701D221035）、山西医科大学博士启动基金（No.03201501）资助项目.

Efficient Synthesis of Unsymmetrical Selenides Promoted by Titanocene Perfluorobutanesulfonate/Zinc Catalytic System

Wang Lingxiao^a, Li Ningbo^a, Wang Haojiang^a, Liu Wen^a, Diao Haipeng^a, Xu Xinhua^b

a Basic Medical College, Shanxi Medical University, Taiyuan 030001;
b College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received:2018-12-19 Revised:2019-02-03 Published:2019-02-22
Contact: 10.6023/cjoc201812033 E-mail:ningboli@sxmu.edu.cn;diaohp@sxmu.edu.cn
Supported by:
Project supported by the the National Natural Science Foundation of China (No. 21802093), the Shanxi Province Science Foundation for Youths (No. 201701D221035), and the PhD Start-up Foundation of Shanxi Medical University (No. 03201501).

1. Efficient Synthesis of Unsymmetrical Selenides Promoted by Titanocene Perfluorobutanesulfonate/Zinc Catalytic System.PDF(3020KB)

Abstract

In the presence of 10 mol% titanocene perfluorobutanesulfonate (1·H₂O·THF), reductive cleavage Se-Se bond by zinc dust (1.2 equiv.) at room temperature led to nucleophilic selenium anion species, which reacted with bromoalkanes to afford unsymmetrical selenides in good to excellent yield using commercial tetrahydrofuran (THF) as solvent under N₂ atmosphere. The possible reaction mechanism is that zinc dust reduces Cp₂Ti^IV(OPf)₂ (Pf=SO₂C₄F₉) to produce Cp₂Ti^ⅢOPf, which reacts with diaryl diselenides to form the intermediate Cp₂Ti^IVSeAr(OPf). Then it further reacts with bromoalkanes to produce unsymmetrical selenides. In this paper, the synthesis of asymmetrical selenides catalyzed by 1·H₂O·THF/Zn system is first reported. This method has the advantages of mild reaction conditions, simple operation and high yield.

Key words: titanocene perfluorobutanesulfonate, zinc dust, diaryl diselenides, bromoalkanes, unsymmetrical selenides

Cite this article

Wang Lingxiao, Li Ningbo, Wang Haojiang, Liu Wen, Diao Haipeng, Xu Xinhua. Efficient Synthesis of Unsymmetrical Selenides Promoted by Titanocene Perfluorobutanesulfonate/Zinc Catalytic System[J]. Chin. J. Org. Chem., 2019, 39(6): 1802-1807.

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茂钛全氟丁基磺酸盐/锌粉体系高效催化不对称单硒醚合成

Efficient Synthesis of Unsymmetrical Selenides Promoted by Titanocene Perfluorobutanesulfonate/Zinc Catalytic System

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