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Synthesis of Cyclopentene Derivatives via Electrochemically Induced Intermolecular Selective (3+2) Annulation
时间:2022-08-31 15:47:21点击量:

        Zhipeng Guan,Shuxiang Zhu,Yayu Ye,Xiangwei Li,Yanlong Liu,Pengjie Wang,Prof. Heng Zhang,Dr. Zhiliang Huang,Prof. Aiwen Lei.Angew. Chem. Int. Ed.(雷爱文,张恒,黄志良)

        Abstract:

        Cyclopentenes are common cores in many natural products, and in bioactive and functional molecules. However, their synthesis remains challenging in terms of harsh conditions, poor selectivity, prefunctionalization of the substrates, over-reliance on volatile activating reagents and the use of noble metals. Herein, we develop an electrochemical mediator-induced intermolecular selective (3+2) annulation of readily available alkenes and alkynes/alkenes, which provides a simple and efficient method for the synthesis of a library of decorated cyclopentenes and cyclopentanes. This protocol features high efficiency, mild reaction conditions, broad substrate scope, good functional group tolerance, and high regioselectivity. Potential applications are demonstrated by gram-scale synthesis as well as the construction of structural diversity and complexity. A preliminary mechanistic investigation was performed, which indicated that an iodine radical and carbon radicals are involved in this transformation.

        全文链接请见:

        https://doi.org/10.1002/anie.202207059