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

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
› Author Affiliations
Further Information

Publication History

Received: 23 December 2014

Accepted after revision: 02 February 2015

Publication Date:
30 March 2015 (online)


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.

Supporting Information

 
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