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Synthesis of β‑Aminoenones via Cross-Coupling of In-Situ-Generated Isocyanides with 1,3-Dicarbonyl Compounds

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journal contribution
posted on 01.08.2018, 15:37 by Xingxing Ma, Yao Zhou, Qiuling Song
An efficient and practical strategy for the synthesis of β-aminoenones from a three-component reaction was developed. Ethyl bromodifluoroacetate serves as a C1 source in this strategy, forming isocyanides in situ with primary amines. This reaction represents the first example of utilization of readily available starting materials to generate isocyanides in situ and sequentially fully converted to β-aminoenones, avoiding the generation of byproduct imines and overinsertion products. The mechanism study suggested that this method involves activation of two C­(sp3)–F bonds and the formation of isocyanides, which might nourish both isocyanide chemistry and fluorine chemistry.