fecl3催化吡咯系缚吲哚的氧化二烯化反应。

IF 2.7 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2025-01-16 DOI:10.1039/d4ob01929f

Jing Zhou , Xue Sheng , Man Jiang , Hai-Lei Cui

{"title":"fecl3催化吡咯系缚吲哚的氧化二烯化反应。","authors":"Jing Zhou , Xue Sheng , Man Jiang , Hai-Lei Cui","doi":"10.1039/d4ob01929f","DOIUrl":null,"url":null,"abstract":"<div><div>A mild and efficient FeCl<sub>3</sub>-catalyzed oxidative diselenylation of pyrrole-tethered indoles has been achieved by using RSeSeR as the source of selenium and <em>m</em>-chloroperoxybenzoic acid (<em>m</em>CPBA) as the oxidant (17–70% yields). In addition, this selenylation reaction system can be expanded to the functionalization of tryptophan derivatives and melatonin at the C-2 position of the indole moiety (55–58% yields).</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 9","pages":"Pages 2254-2262"},"PeriodicalIF":2.7000,"publicationDate":"2025-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"FeCl3-catalyzed oxidative diselenylation of pyrrole-tethered indoles†\",\"authors\":\"Jing Zhou , Xue Sheng , Man Jiang , Hai-Lei Cui\",\"doi\":\"10.1039/d4ob01929f\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A mild and efficient FeCl<sub>3</sub>-catalyzed oxidative diselenylation of pyrrole-tethered indoles has been achieved by using RSeSeR as the source of selenium and <em>m</em>-chloroperoxybenzoic acid (<em>m</em>CPBA) as the oxidant (17–70% yields). In addition, this selenylation reaction system can be expanded to the functionalization of tryptophan derivatives and melatonin at the C-2 position of the indole moiety (55–58% yields).</div></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\"23 9\",\"pages\":\"Pages 2254-2262\"},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2025-01-16\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S147705202500062X\",\"RegionNum\":3,\"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 & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S147705202500062X","RegionNum":3,"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

以RSeSeR为硒源，间氯过氧苯甲酸（mCPBA）为氧化剂，实现了fec_3温和高效的吡咯系缚吲哚氧化二烯化反应（产率17-70%）。此外，该硒化反应体系可以扩展到吲哚部分C-2位置的色氨酸衍生物和褪黑素的功能化（产率55-58%）。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

FeCl3-catalyzed oxidative diselenylation of pyrrole-tethered indoles†

查看原文本刊更多论文

FeCl3-catalyzed oxidative diselenylation of pyrrole-tethered indoles†

A mild and efficient FeCl₃-catalyzed oxidative diselenylation of pyrrole-tethered indoles has been achieved by using RSeSeR as the source of selenium and m-chloroperoxybenzoic acid (mCPBA) as the oxidant (17–70% yields). In addition, this selenylation reaction system can be expanded to the functionalization of tryptophan derivatives and melatonin at the C-2 position of the indole moiety (55–58% yields).

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 & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.