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General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP

Xingjie Zhang, Aiyou Xia, Haoyi Chen and Yuanhong Liu*

*Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, People’s Republic of China, Email: yhliusioc.ac.cn

X. Zhang, A. Xia, H. Chen, Y. Liu, Org. Lett., 2017, 19, 2118-2121.

DOI: 10.1021/acs.orglett.7b00732 (free Supporting Information)


Abstract

A general catalyzed cyanation of hetero(aryl) chlorides using less toxic Zn(CN)2 as the cyanide source relies on the use of inexpensive NiCl26H2O/dppf/Zn as the catalytic system and DMAP as additive. The cyanation occurs under mild reaction conditions with wide functional group tolerance. The method was also successfully extended to aryl bromides and aryl iodides.

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Key Words

cyanation


ID: J54-Y2017