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Electrochemical Oxidation Dearomatization of Anisol Derivatives toward Spiropyrrolidines and Spirolactones

CCS Chemistry 2022年第4期4卷 1199-1207页

作者： Cui Zhang faxiang bu Chulin Zeng Dan Wang Lijun Lu Heng Zhang Aiwen Lei College of Chemistry and Molecular Sciences Institute for Advanced Studies(IAS)Wuhan UniversityWuhanHubei 430072 State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032

Spiro compounds are widely prevalent in biological activities and natural products.However,developing new strategies for their efficient synthesis and derivatization remains a challenge.Outstanding progress has been made in the synthesis of spiro compounds through dearomatization of aromatic compounds,most of them are mediated by the hypervalent iodine reagents.Herein,we report a method of anodic oxidation spiroamination and spirolactonization of anisole derivatives with concomitant cathodic reduction of protons in the absence of hypervalent iodine reagents.A wide variety of spiropyrrolidines and spirolactones with diverse functional groups made useful scaffolds in this transformation,with yields up to 97%.Moreover,hectogram-scale synthesis could supply target product with 83% yield in a flow electrochemical cell using carbon paper as the anode and nickel plate as the cathode,demonstrating the potential application of this method.

关键词： electrochemical spiropyrrolidine spirolactone dearomatization spiro-cycle anisole derivatives hectogram synthesis flow cell

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Facile and Economical Electrochemical Dehalogenative Deuteration of(Hetero)Aryl Halides

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CCS Chemistry 2021年第11期3卷 2669-2675页

作者： Lijun Lu Hao Li Yifan Zheng faxiang bu Aiwen Lei Institute for Advanced Studies(IAS) College of Chemistry and Molecular SciencesWuhan UniversityWuhan 430072 National Research Center for Carbohydrate Synthesis Jiangxi Normal UniversityJiangxi 330022

Deuterated compounds are valuable in synthetic,pharmaceutical,and analytical chemistry.The deuteration of halides is a widespread method for highly site-selective deuterium installation.However,the facile,efficient,and economical deuterium incorporation remains challenging.In this work,we introduced a practical deuteration of(hetero)aryl halides through an electrochemical reduction method.This transformation proceeded smoothly at room temperature without metal catalysts,external reductants,or toxic or dangerous reagents.Remarkably,low-cost and chemically equivalent D2O was the sole deuterium source in this reaction.Professional electrosynthesis equipment was not essential because we demonstrated common batteries and electrodes were enough for this reaction.

关键词： electrochemical synthesis deuteration dehalogenation aryl halides deuterium oxide

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