Electrochemical Reduction of Cinnamonitrile in the Presence of Carbon Dioxide: Synthesis of Cyano- and Phenyl-Substituted Propionic Acids

Huan Wang; Mei-Yu Lin; Kai Zhang; Su-Jiao Li; Jia-Xing Lu

doi:10.1071/CH08092

RESEARCH ARTICLE

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Electrochemical Reduction of Cinnamonitrile in the Presence of Carbon Dioxide: Synthesis of Cyano- and Phenyl-Substituted Propionic Acids

Huan Wang ^A , Mei-Yu Lin ^A , Kai Zhang ^A , Su-Jiao Li ^A and Jia-Xing Lu ^A ^B

+ Author Affiliations

- Author Affiliations

^A Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062, China.

^B Corresponding author. Email: jxlu@chem.ecnu.edu.cn

Australian Journal of Chemistry 61(7) 526-530 https://doi.org/10.1071/CH08092
Submitted: 4 March 2008 Accepted: 16 April 2008 Published: 16 July 2008

Abstract

Cyano- and phenyl-substituted propionic acids were synthesized simply and efficiently by electrocarboxylation of cinnamonitrile in undivided cells using the non-noble metal nickel as cathode and magnesium as the anode. The radical anion generated by the electroreduction of cinnamonitrile in the absence of CO₂ is involved in several competitive reactions that lead to the formation of linear hydrodimers, cyclic hydrodimers, saturated dihydro products, and glutaronitrile derivatives. While under 101.325 kPa of CO₂, the electrocarboxylation could easily be carried out in the absence of additional catalysts, and with good yield (84.8%). The influence of various synthetic parameters, such as the nature of the electrode, the working potential, the concentration, and the temperature, on the electrocarboxylation reaction was investigated.

Acknowledgements

The present work was supported by the National Natural Science Foundation of China (no. 20573037), the Natural Science Foundation of Shanghai (no. 05JC1470), a Shanghai Leading Academic Discipline Project (B409), and PhD Program Scholarship Fund of ECNU 2007.

References

Electrochemical Reduction of Cinnamonitrile in the Presence of Carbon Dioxide: Synthesis of Cyano- and Phenyl-Substituted Propionic Acids

Abstract

Acknowledgements

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