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AgI-PEG400-KI Catalyzed Environmentally Benign Synthesis of Aroyl Cyanides Using Potassium Hexacyanoferrate(II) as the Cyanating Agent

Zheng Li*, Shengyi Shi, Jingya Yang

*Gansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China, Email: lizhengnwnu.edu.cn

Z. Li, S. Shi, J. Yang, Synlett, 2006, 2495-2497.

DOI: 10.1055/s-2006-950407


Abstract

A practical cyanation of aroyl chlorides was performed in DMF at room temperature with 0.2 equivalent of a non-toxic cyanide source, 3 mol% AgI, 4 mol% PEG-400, and 3 mol% KI as the catalyst system. The corresponding aroyl cyanides were prepared in good yields.


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Details

The document describes an environmentally friendly method for synthesizing aroyl cyanides using potassium hexacyanoferrate(II) (K4[Fe(CN)6]) as a non-toxic cyanide source. The reaction is catalyzed by a system comprising 3 mol% AgI, 4 mol% PEG400, and 3 mol% KI in DMF at room temperature, yielding aroyl cyanides in 64-89% within eight to ten hours. This method avoids the use of highly toxic metal cyanides and moisture-sensitive trimethylsilyl cyanide, making it safer and more practical. The AgI catalyst enhances the reaction rate by promoting the release of cyanide ions from (K4[Fe(CN)6]), while PEG400 acts as a phase-transfer catalyst, and KI improves the solubility of AgI and facilitates nucleophilic substitution. The method is effective for various aroyl chlorides, including those with electron-withdrawing or electron-donating groups, and even heteroaroyl chlorides like 2-furoyl and 2-thiophenecarbonyl chlorides. The reactions are conducted under anhydrous conditions to prevent hydrolysis and ensure high yields. This study demonstrates a significant advancement in the synthesis of aroyl cyanides, offering a greener and more efficient alternative to traditional methods.


Key Words

green chemistry, catalysis, synthesis, phase-transfer catalysis, cyanation


ID: J60-Y2006-4650