可见光驱动Benzylic C(sp3) -H羧基化可以用13c -甲酸合成13c标记的（±）-α-氨基酸

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-09-08 DOI:10.1021/acs.orglett.5c03238

Hao Zhang, Xiao-Yang Wu, Pan-Pan Gao, Zhu Li, Shangde Ai, Yang-Tong Ma, Zhuofan Jian and Gang Li*,

{"title":"可见光驱动Benzylic C(sp3) -H羧基化可以用13c -甲酸合成13c标记的（±）-α-氨基酸","authors":"Hao Zhang, Xiao-Yang Wu, Pan-Pan Gao, Zhu Li, Shangde Ai, Yang-Tong Ma, Zhuofan Jian and Gang Li*, ","doi":"10.1021/acs.orglett.5c03238","DOIUrl":null,"url":null,"abstract":"13C-labeled α-amino acids are important molecules in biological studies and drug development. Cost-effective synthesis of α-amino acids with a high level of 13C incorporation under mild conditions remains limited. Herein, we report the development of a benzylic C(sp3)–H carboxylation method to prepare highly 13C-labeled α-amino acids, i.e., arylglycines, using near-stoichiometric and user-friendly sodium 13C-formate. The sequential reaction pathway of in situ 13C-carbon dioxide (CO2) generation followed by C–H carboxylation via 1,2-HAT was suggested by mechanistic studies.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 37","pages":"10435–10441"},"PeriodicalIF":5.0000,"publicationDate":"2025-09-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible Light-Driven Benzylic C(sp3)–H Carboxylation Enables Synthesis of 13C-Labeled (±)-α-Amino Acids with 13C-Formate\",\"authors\":\"Hao Zhang, Xiao-Yang Wu, Pan-Pan Gao, Zhu Li, Shangde Ai, Yang-Tong Ma, Zhuofan Jian and Gang Li*, \",\"doi\":\"10.1021/acs.orglett.5c03238\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"13C-labeled α-amino acids are important molecules in biological studies and drug development. Cost-effective synthesis of α-amino acids with a high level of 13C incorporation under mild conditions remains limited. Herein, we report the development of a benzylic C(sp3)–H carboxylation method to prepare highly 13C-labeled α-amino acids, i.e., arylglycines, using near-stoichiometric and user-friendly sodium 13C-formate. The sequential reaction pathway of in situ 13C-carbon dioxide (CO2) generation followed by C–H carboxylation via 1,2-HAT was suggested by mechanistic studies.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"27 37\",\"pages\":\"10435–10441\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-09-08\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.orglett.5c03238\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.5c03238","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

13c标记α-氨基酸是生物学研究和药物开发中的重要分子。在温和条件下，高水平13C掺入的α-氨基酸的低成本合成仍然有限。在此，我们报告了一种苯基C(sp3) -H羧化方法的发展，以制备高度13c标记的α-氨基酸，即芳基甘氨酸，使用近化学计量学和用户友好的13c -甲酸钠。机理研究提出了原位13c - CO2 （CO2）生成后通过1,2- hat进行C-H羧化的顺序反应途径。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Visible Light-Driven Benzylic C(sp3)–H Carboxylation Enables Synthesis of 13C-Labeled (±)-α-Amino Acids with 13C-Formate

查看原文本刊更多论文

Visible Light-Driven Benzylic C(sp3)–H Carboxylation Enables Synthesis of 13C-Labeled (±)-α-Amino Acids with 13C-Formate

¹³C-labeled α-amino acids are important molecules in biological studies and drug development. Cost-effective synthesis of α-amino acids with a high level of ¹³C incorporation under mild conditions remains limited. Herein, we report the development of a benzylic C(sp³)–H carboxylation method to prepare highly ¹³C-labeled α-amino acids, i.e., arylglycines, using near-stoichiometric and user-friendly sodium ¹³C-formate. The sequential reaction pathway of in situ ¹³C-carbon dioxide (CO₂) generation followed by C–H carboxylation via 1,2-HAT was suggested by mechanistic studies.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.