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光促进吡啶酮和相关 - 杂芳环的固有三氟甲基化反应。

A Light-Promoted Innate Trifluoromethylation of Pyridones and Related -Heteroarenes.

机构信息

Department of Chemistry and Biochemistry, San Diego State University, 5500 Campanile Drive, San Diego, California 92182-1030, United States.

出版信息

Org Lett. 2023 Jul 7;25(26):4898-4902. doi: 10.1021/acs.orglett.3c01710. Epub 2023 Jun 28.

Abstract

We report a practical, light-mediated perfluoroalkylation using Langlois' reagent (sodium trifluoromethylsulfinate) that proceeds in the absence of any photocatalyst or additives. This method has allowed for the facile functionalization of pyridones and related -heteroarenes such as azaindole. This protocol is operationally simple, uses readily available materials, and is tolerable for electron-neutral and -rich functional pyridones. Cyclic voltammetry was utilized as a mechanistic probe, and preliminary data suggest the reaction may involve an electrophilic radical mechanism.

摘要

我们报告了一种实用的、受光介导的全氟烷基化反应,使用 Langlois 试剂(三氟甲基亚磺酸钠)在没有任何光催化剂或添加剂的情况下进行。该方法可以方便地对吡啶酮和相关的杂芳环,如氮杂吲哚进行功能化。该方案操作简单,使用易得的材料,对电子中性和富电子的功能化吡啶酮具有耐受性。循环伏安法被用作一种机理探针,初步数据表明该反应可能涉及亲电自由基机理。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/85d7/10334463/361903a04563/ol3c01710_0001.jpg

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