A Mild and Efficient Palladium-Catalyzed Cyanation of Aryl Chlorides with K₄[Fe(CN)₆]

Pui Yee Yeung, Chau Ming So, Chak Po Lau and Fuk Yee Kwong*

*State Key Laboratory of Chirosciences and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, Email: bcfykinet.polyu.edu.hk

P. Y. Yeung, C. M. So, C. P. Lau, F. Y. Kwong, Org. Lett., 2011, 13, 648-651.

DOI: 10.1021/ol1028892

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Abstract

In the presence of a highly effective Pd/CM-phos catalyst, an efficient cyanation of aryl chlorides proceeds at 70°C in general. Common functional groups such as keto, aldehyde, ester, nitrile and -NH₂, and heterocyclic coupling partners are well tolerated. Moreover, a sterically hindered nonactivated ortho,ortho-disubstituted electrophile is shown to be a feasible coupling partner in cyanation.

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Key Words

Cyanation

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ID: J54-Y2011-0360