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通过铜催化肟乙酸酯的N-O裂解实现氟烷基化吡啶和2-吡啶酮的氧化还原发散合成

Redox-Divergent Synthesis of Fluoroalkylated Pyridines and 2-Pyridones through Cu-Catalyzed N-O Cleavage of Oxime Acetates.

作者信息

Bai Dachang, Wang Xueli, Zheng Guangfan, Li Xingwei

机构信息

Henan Key Laboratory of Organic Functional Molecules and Drugs Innovation, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, 453007, China.

Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China.

出版信息

Angew Chem Int Ed Engl. 2018 May 28;57(22):6633-6637. doi: 10.1002/anie.201802311. Epub 2018 Apr 26.

DOI:10.1002/anie.201802311
PMID:29604154
Abstract

Cu-catalyzed redox-divergent [3+3] coupling of oxime esters with β-CF enones and acrylates is described. This redox-neutral coupling with enones and acrylates affords trifluoromethylated pyridines and pyridones, respectively. Under reductive conditions, difluoromethylated pyridines, difluoromethlated pyridones, and trifluoromethylated dihydropyridones are obtained. The reactions occur under mild conditions with broad substrate scope and regio/redox selectivity.

摘要

描述了铜催化的肟酯与β-三氟甲基烯酮和丙烯酸酯的氧化还原发散型[3+3]偶联反应。这种与烯酮和丙烯酸酯的氧化还原中性偶联反应分别得到三氟甲基化吡啶和吡啶酮。在还原条件下，可得到二氟甲基化吡啶、二氟甲基化吡啶酮和三氟甲基化二氢吡啶。该反应在温和条件下进行，底物范围广，具有区域/氧化还原选择性。

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