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Homogeneous and Stereoselective Copper(II)-Catalyzed Monohydration of Methylenemalononitriles to 2-Cyanoacrylamides

Xiaoqing Xin, Dexuan Xiang, Jiming Yang, Qian Zhang, Fenguo Zhou and Dewen Dong*

*Laboratory of Green Chemistry and Process, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022 Jilin, People's Republic of China, Email:

X. Xin, D. Xiang, J. Yang, Q. Zhang, F. Zhou, D. Dong, J. Org. Chem., 2013, 78, 11956-11961.

DOI: 10.1021/jo401997v

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A facile and efficient route for the homogeneous and highly stereoselective monohydration of substituted methylenemalononitriles to (E)-2-cyanoacrylamides is catalyzed by copper(II) acetate in acetic acid containing 2% water. The protocol is suitable for the monohydration of dicyanobenzenes and 2-substituted malononitriles.

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ID: J42-Y2013