Electrochemical Oxidation Dearomatization of Anisol Derivatives toward Spiropyrrolidines and Spirolactones  

作　　者：Cui Zhang Faxiang Bu Chulin Zeng Dan Wang Lijun Lu Heng Zhang Aiwen Lei 

机构地区：[1]College of Chemistry and Molecular Sciences,Institute for Advanced Studies(IAS),Wuhan University,Wuhan,Hubei 430072 [2]State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032

出　　处：《CCS Chemistry》2022年第4期1199-1207,共9页中国化学会会刊（英文）

基　　金：supported by the National Natural Science Foundation of China(no.22031008);the Science Foundation of Wuhan(no.2020010601012192).

摘　　要：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 

分 类 号：O62[理学—有机化学]