使用 N-杂环碳烯盐作为 C1 前体合成双(吲哚基)甲烷。

IF 2.7 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2024-10-16 DOI:10.1039/d4ob01568a

Bingwei Zhou , Zhao Gao , Yanhao Yang , Yuanyuan Hu

{"title":"使用 N-杂环碳烯盐作为 C1 前体合成双(吲哚基)甲烷。","authors":"Bingwei Zhou , Zhao Gao , Yanhao Yang , Yuanyuan Hu","doi":"10.1039/d4ob01568a","DOIUrl":null,"url":null,"abstract":"<div><div>We herein describe an alkylation reaction of indoles with NHC salts to access bis(indolyl)methanes as product. The NHC salt (or free NHC) serves as a C1 precursor due to decomposition of its N-heterocyclic ring. Although the exact roles of zinc powder and acetic/formic acid remain elusive, both of them are indispensable for this reaction. Two possible reaction pathways are proposed based on the results of mechanistic experiments.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"22 46","pages":"Pages 9058-9062"},"PeriodicalIF":2.7000,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of bis(indolyl)methanes using N-heterocyclic carbene salt as a C1 precursor†\",\"authors\":\"Bingwei Zhou , Zhao Gao , Yanhao Yang , Yuanyuan Hu\",\"doi\":\"10.1039/d4ob01568a\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>We herein describe an alkylation reaction of indoles with NHC salts to access bis(indolyl)methanes as product. The NHC salt (or free NHC) serves as a C1 precursor due to decomposition of its N-heterocyclic ring. Although the exact roles of zinc powder and acetic/formic acid remain elusive, both of them are indispensable for this reaction. Two possible reaction pathways are proposed based on the results of mechanistic experiments.</div></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\"22 46\",\"pages\":\"Pages 9058-9062\"},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2024-10-16\",\"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/S1477052024009182\",\"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/S1477052024009182","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

我们在此介绍吲哚与 NHC 盐的烷基化反应，以获得双(吲哚基)甲烷作为产物。NHC 盐（或游离 NHC）因其 N-杂环的分解而成为 C1 前体。虽然锌粉和乙酸/甲酸的确切作用仍难以确定，但它们在该反应中都是不可或缺的。根据机理实验的结果，提出了两种可能的反应途径。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Synthesis of bis(indolyl)methanes using N-heterocyclic carbene salt as a C1 precursor†

查看原文本刊更多论文

Synthesis of bis(indolyl)methanes using N-heterocyclic carbene salt as a C1 precursor†

We herein describe an alkylation reaction of indoles with NHC salts to access bis(indolyl)methanes as product. The NHC salt (or free NHC) serves as a C1 precursor due to decomposition of its N-heterocyclic ring. Although the exact roles of zinc powder and acetic/formic acid remain elusive, both of them are indispensable for this reaction. Two possible reaction pathways are proposed based on the results of mechanistic experiments.

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.