Organo-electroreduction enables arylcarboxylation of styrenes  

作　　者：Yanwei Wang Qian Wang Zile Zhu Weikang Qi Youai Qiu 

机构地区：[1]State Key Laboratory and Institute of Elemento-Organic Chemistry,Frontiers Science Center for New Organic Matter,Haihe Laboratory of Sustainable Chemical Transformations,College of Chemistry,Nankai University,Tianjin 300071,China

出　　处：《Science China Chemistry》2024年第11期3825-3832,共8页中国科学（化学英文版）

基　　金：supported by the National Key R&D Program of China (2022YFA1503200);the National Natural Science Foundation of China (22371149, 22301144, 22188101);the Fundamental Research Funds for the Central Universities (63223015);the Frontiers Science Center for New Organic Matter, Nankai University (63181206);Nankai University;the Haihe Laboratory of Sustainable Chemical Transformations for financial support。

摘　　要：Electroreduction offers an alternative to generate high active intermediates from electrophiles(halides, alkenes, etc.) in organic synthesis. However, it still remains challenge to enable the transformations in controlled fashion for substrates with similar reduction potentials. Herein, an electroreductive arylcarboxylation of styrenes with aryl halides and CO_(2)promoted by an organomediator has been developed. The reaction exhibits the remarkable reactivity control between styrenes and aryl halides bearing very similar reduction potentials, which is enabled by the addition of a simple organic mediator. The mediated process for different kinds of aryl halides(iodides and bromides) could be achieved by simply tuning the electronic effect of the skeleton of naphthalene. This protocol displays a broad substrate scope and the extension to late-stage modification of biorelevant molecules and their derivatives showed a bright prospect. Moreover, density functional theory(DFT) calculations and mechanistic studies have been conducted and provide solid support to rationalize the selectivity and reactivity control observed.

关 键 词：CO_(2)utilization reductive organo-mediator CARBOXYLATION ELECTROREDUCTION aryl halides 

分 类 号：O621.251[理学—有机化学]