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Synlett 2004(10): 1776-1778  
DOI: 10.1055/s-2004-829569
LETTER
© Georg Thieme Verlag Stuttgart · New York

Inorganic/Organic Salts as Heterogeneous Basic Catalysts for Cyanosilylation of Carbonyl Compounds

Bin Hea, Yan Lia, Xiaoming Feng*a,b, Guolin Zhangc
a Key Laboratory of Green Chemistry & Technology (Sichuan University), Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China
Fax: +86(28) 85418249; e-Mail: xmfeng@scu.edu.cn;
b State Key Laboratory of Applied Organic Chemistry, Lanzhou 730000, P. R. China
c Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, P. R. China
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Publication History

Received 16 May 2004
Publication Date:
28 July 2004 (online)

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Abstract

The addition of TMSCN to carbonyl compounds catalyzed by K2CO3 as heterogeneous catalyst gave the corresponding cyanohydrin trimethylsilyl ethers from 20 minutes to 24 hours with 62% to 99% yields without solvent at room temperature. Moreover, it was found that chiral organic salts as heterogeneous catalysts also can catalyze the asymmetric version and afford the corresponding products with up to 99% yield and 12.4% ee.

Key words

heterogeneous catalysis - potassium carbonate - cyano­silylation - cyanohydrins - carbonyl compounds

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A series of solvents was screened including toluene, CH2Cl2, Et2O and THF.

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General Procedures for Cyanosilylation of Carbonyl Compounds: To a mixture of carbonyl compound (2 mmol) and K2CO3 (8 mg, 0.06 mmol for aldehydes or 83 mg, 0.60 mmol for ketones) was added trimethylsilyl cyanide (328 µL, 2.40 mmol) at r.t. The reaction was monitored by TLC. After the reaction period described in Table [1] , K2CO3 was filtrated from the reaction mixture and the residues were purified by flash chromatography to give the products, which were determined by 1H NMR spectroscopy.