在催化量有机介质存在下有机卤化物的无金属电化学羧化反应
Metal-Free Electrochemical Carboxylation of Organic Halides in the Presence of Catalytic Amounts of an Organomediator.
作者信息
Wang Yanwei, Zhao Zhiwei, Pan Deng, Wang Siyi, Jia Kangping, Ma Dengke, Yang Guoqing, Xue Xiao-Song, Qiu Youai
机构信息
State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071, China.
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
出版信息
Angew Chem Int Ed Engl. 2022 Oct 10;61(41):e202210201. doi: 10.1002/anie.202210201. Epub 2022 Sep 8.
Herein, an electroreductive carboxylation of organic carbon-halogen bonds (X=Br and Cl) promoted by catalytic amounts of naphthalene as an organic mediator is reported. This transformation proceeds smoothly under mild conditions with a broad substrate scope of 59 examples, affording the valuable and versatile carboxylic acids in moderate to excellent yields without the need of costly transition metal, wasted stoichiometric metal reductants, or sacrificial anodes. Further late-stage carboxylations of natural product and drug derivatives demonstrate its synthetic utility. Mechanistic studies confirmed the activation of carbon-halogen bonds via single-electron transfer and the key role of naphthalene in this reaction.
本文报道了一种以催化量的萘作为有机介质促进的有机碳-卤键（X = Br和Cl）的电还原羧化反应。该转化在温和条件下顺利进行，底物范围广泛，有59个实例，无需昂贵的过渡金属、化学计量的金属还原剂或牺牲阳极，就能以中等至优异的产率得到有价值且用途广泛的羧酸。天然产物和药物衍生物的进一步后期羧化反应证明了其合成实用性。机理研究证实了通过单电子转移激活碳-卤键以及萘在该反应中的关键作用。
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