Me3SiCl-Promoted Conjugate Hydrocyanation of α,β-Unsaturated Ketones Using Potassium Hexacyanoferrate(II) as Cyanide Source

doi:10.6023/cjoc201501019

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (6): 1286-1293.DOI: 10.6023/cjoc201501019 Previous Articles Next Articles

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Me₃SiCl促进亚铁氰化钾为氰源的α,β-不饱和酮的共轭氢氰化

杨靖亚, 占宝华, 马奔, 向现成, 保云芬, 李政

西北师范大学化学化工学院兰州 730070

收稿日期:2015-01-15 修回日期:2015-01-27 发布日期:2015-02-05
通讯作者: 杨靖亚 E-mail:yangjy@nwnu.edu.cn
基金资助:
国家自然科学基金(Nos. 21362034, 21162026)、高等学校博士学科点专项科研基金(No. 20136203120005)和甘肃省高等学校科研(No. 2013B-003)资助项目.

Me₃SiCl-Promoted Conjugate Hydrocyanation of α,β-Unsaturated Ketones Using Potassium Hexacyanoferrate(II) as Cyanide Source

Yang Jingya, Zhan Baohua, Ma Ben, Xiang Xiancheng, Bao Yunfen, Li Zheng

College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received:2015-01-15 Revised:2015-01-27 Published:2015-02-05
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21362034 and 21162026), the Research Fund for the Doctoral Program of Higher Education of China (No. 20136203120005) and the University Scientific Research Project of Gansu Province (No. 2013B-003).

1. Me₃SiCl-Promoted Conjugate Hydrocyanation of α,β-Unsaturated Ketones Using Potassium Hexacyanoferrate(II) as Cyanide Source.PDF(2409KB)

Abstract

A Me₃SiCl-promoted conjugate hydrocyanation of α,β-unsaturated ketones using non-toxic potassium hexacyanoferrate(II) as an eco-friendly cyanide source is described. By "one-pot" procedure, the intermediate, trimethylsilyl cyanide, does not need separation. With 1 mol% Cs₂CO₃ as catalyst, a variety of aromatic and aliphatic α,β-unsaturated ketones afforded the corresponding β-cyano ketones regioselectivity exclusively. Avoiding the traditional highly toxic cyanide and without separation of the reactive intermediate trimethylsilyl cyanide make this protocol more practical.

Key words: Michael addition, cyanides, α,β-unsaturated ketones, green chemistry, potassium hexacyanoferrate(II)

Cite this article

Yang Jingya, Zhan Baohua, Ma Ben, Xiang Xiancheng, Bao Yunfen, Li Zheng. Me₃SiCl-Promoted Conjugate Hydrocyanation of α,β-Unsaturated Ketones Using Potassium Hexacyanoferrate(II) as Cyanide Source[J]. Chin. J. Org. Chem., 2015, 35(6): 1286-1293.

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Me₃SiCl促进亚铁氰化钾为氰源的α,β-不饱和酮的共轭氢氰化

Me₃SiCl-Promoted Conjugate Hydrocyanation of α,β-Unsaturated Ketones Using Potassium Hexacyanoferrate(II) as Cyanide Source

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Me3SiCl促进亚铁氰化钾为氰源的α,β-不饱和酮的共轭氢氰化