Chinese Journal of Organic Chemistry >
Me3SiCl-Promoted Conjugate Hydrocyanation of α,β-Unsaturated Ketones Using Potassium Hexacyanoferrate(II) as Cyanide Source
Received date: 2015-01-15
Revised date: 2015-01-27
Online 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).
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.
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]. Chinese Journal of Organic Chemistry, 2015 , 35(6) : 1286 -1293 . DOI: 10.6023/cjoc201501019
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