Highly Efficient Michael Reactions of Nitroolefins by Grinding Means

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Author(s): Dong-Xiao Cui, Yue-Dan Li, Jun-Chao Zhu, Yan-Yan Jia, Ai-Dong Wen*, Ping-An Wang*.

Journal Name: Current Organic Synthesis

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Aims and Objectives: The direct β-functionalization of trans-β-nitroolefins by Michael reaction is regarded as an efficient way to provide precursors for β-functional amines. However, Michael additions by grinding means with solvent-free conditons are rarely reported. We have developed a facile access to β-functional nitroalkanes by grinding means under solvent-free conditions.

Material and Method: From commercially available materails including ethyl 2-nitroacetate, alkyl 2-cyanoacetates and malononitrile, the grinding reactions between these above-mentioned activated methylene-compounds and various trans-β-nitroolefins were performed at room temperature and solvent-free conditions.

Results: A highly efficient direct Michael reaction of nitroolefins by simple grinding means has been developed. Various trans-nitrostyrenes were easily converted into corresponding β-functional nitroalkanes in excellent yields within 5~10 min (up to 36 examples).

Conclusion: Herein, we have developed a simple and efficient way to β-functional nitroalkanes through Michael reactions by grinding means. These grinding Michael reactions enjoy fast, clean and stable and these Michael adducts could be easily converted into the other amino compounds served as building blocks in organic synthesis.

Keywords: Michael reaction, nitroolefin, grinding, catalyst-free, nitroalkane, β-functional nitroalkanes

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(E-pub Ahead of Print)
DOI: 10.2174/1570179416666190101122150
Price: $95

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