Synthesis 2015; 47(11): 1560-1566
DOI: 10.1055/s-0034-1379899
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium/N-Heterocyclic Carbene Catalyzed Mono- and Double-Cyanation of Aryl Halides Using Potassium Ferrocyanide Trihydrate under Aerobic Conditions

Authors

  • Zhicheng Xu

    a   School of Chemistry and Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. of China
  • Yunqing Xiao

    a   School of Chemistry and Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. of China
  • Hong Ding

    b   State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun, Jilin 130012, P. R. of China   eMail: yhshi@jsnu.edu.cn
  • Changsheng Cao*

    a   School of Chemistry and Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. of China
  • Haitao Li

    a   School of Chemistry and Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. of China
  • Guangsheng Pang

    b   State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun, Jilin 130012, P. R. of China   eMail: yhshi@jsnu.edu.cn
  • Yanhui Shi*

    a   School of Chemistry and Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. of China
Weitere Informationen

Publikationsverlauf

Received: 23. Dezember 2014

Accepted after revision: 02. Februar 2015

Publikationsdatum:
30. März 2015 (online)


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Abstract

A practical palladium/N-heterocyclic carbene catalyzed procedure for the mono- and double-cyanation of aryl halides is described using inexpensive, easy-to-handle and nontoxic potassium ferrocyanide trihydrate {K4[Fe(CN)6]·3H2O} as the cyanating agent. The reaction does not require an anhydrous solvent, or the exclusion of air or moisture. A variety of electron-rich and electron-deficient aryl halides are efficiently converted into their corresponding nitriles and dicarbonitriles.

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