Dual nickel/photoredox catalyzed carboxylation of C(sp2)-halides with formate†

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 ,&nbsp;Jia-Xin Wang ,&nbsp;Wei Ge ,&nbsp;Fang-Ming Du ,&nbsp;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.

Abstract Image

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
双镍/光氧化还原催化C(sp2)-卤化物与甲酸†的羧化反应
在此,我们报道了一种高效实用的方案,通过在镍介导的键形成过程中与CO2自由基阴离子结合,用甲酸盐对C(sp2)-卤化物进行脱卤羧化。多种具有不同官能团的芳基碘化物、芳基溴化物和链烯基溴化物通过可见光-光还原镍双催化顺利进行反应。几种13C标记的药物中间体的合成和商业药物的克级合成突出了该方法在药物发现环境中的合成价值。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
CiteScore
7.80
自引率
0.00%
发文量
0
期刊最新文献
Clean and economic synthesis of N-sulfonyl isothioureas from isocyanides, sulfonamides and disulfides Core-modified N-confused pentaphyrin variants with adaptive (anti)aromaticity Facile N-directed Ru-catalyzed C(3)–H acylation of heterocyclopentadienes with acyl chlorides AgOTf-promoted transetherification of p-methoxybenzyl ethers with allyl and benzyl bromides 1,6-Hydrosulfonylation of p-quinone methides enabled via strain-release-/aromaticity-driven alkyl radical generation and SO2-capture: synthesis and antiproliferative studies of sulfonylated diarylmethanes
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1