Ming-Chen Fu , Jia-Xin Wang , Wei Ge , Fang-Ming Du , Yao Fu
{"title":"Dual nickel/photoredox catalyzed carboxylation of C(sp2)-halides with formate†","authors":"Ming-Chen Fu , Jia-Xin Wang , Wei Ge , Fang-Ming Du , Yao Fu","doi":"10.1039/d2qo01361d","DOIUrl":null,"url":null,"abstract":"<div><p>Herein, we report an efficient and practical protocol for dehalocarboxylation of C(sp<sup>2</sup>)-halides with formate by the engagement of a CO<sub>2</sub> radical anion in a nickel-mediated bond-forming process. A wide variety of aryl iodides, aryl bromides, and alkenyl bromides bearing a diverse set of functional groups underwent the reaction smoothly through visible-light photoredox nickel dual catalysis. The synthesis of several <sup>13</sup>C-labeled drug intermediates and the gram-scale synthesis of commercial drugs highlight the synthetic value of the approach in drug discovery settings.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 1","pages":"Pages 35-41"},"PeriodicalIF":0.0000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"3","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052411023003231","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 3
Abstract
Herein, we report an efficient and practical protocol for dehalocarboxylation of C(sp2)-halides with formate by the engagement of a CO2 radical anion in a nickel-mediated bond-forming process. A wide variety of aryl iodides, aryl bromides, and alkenyl bromides bearing a diverse set of functional groups underwent the reaction smoothly through visible-light photoredox nickel dual catalysis. The synthesis of several 13C-labeled drug intermediates and the gram-scale synthesis of commercial drugs highlight the synthetic value of the approach in drug discovery settings.