铜烯碳酰胺：通过重氮烯醛和 N-取代的吡咯之间的 [4+2] 苯并annulation 快速获得 1,7-二取代的吲哚

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Accounts of Chemical Research Pub Date : 2024-10-19 DOI:10.1016/j.tetlet.2024.155331

Bapurao Sudam Lad, Pratap Kumar Mandal, Rahul Chakrawarti, Sreenivas Katukojvala

{"title":"铜烯碳酰胺：通过重氮烯醛和 N-取代的吡咯之间的 [4+2] 苯并annulation 快速获得 1,7-二取代的吲哚","authors":"Bapurao Sudam Lad, Pratap Kumar Mandal, Rahul Chakrawarti, Sreenivas Katukojvala","doi":"10.1016/j.tetlet.2024.155331","DOIUrl":null,"url":null,"abstract":"<div><div>A highly electrophilic copper enalcarbenoid has been disclosed here for the first time for its carbenoid reactivity. The synthetic utility of the transient Cu-enalcarbenoids has been demonstrated in the Cu-catalyzed direct synthesis of 1,7-disubstituted indoles from diazoenals and <em>N</em>-substituted pyrroles. In this reaction, Cu-enalcarbenoid served as a 4[C] biselectrophilic synthon whereas pyrrole served as a 2[C] bisnucleophilie leading to [4+2] benzannulation.</div></div>","PeriodicalId":1,"journal":{"name":"Accounts of Chemical Research","volume":null,"pages":null},"PeriodicalIF":16.4000,"publicationDate":"2024-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Copper-enalcarbenoids: Rapid access to 1,7-disubstituted indoles via [4+2] benzannulation between diazoenals and N-substituted pyrroles\",\"authors\":\"Bapurao Sudam Lad, Pratap Kumar Mandal, Rahul Chakrawarti, Sreenivas Katukojvala\",\"doi\":\"10.1016/j.tetlet.2024.155331\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A highly electrophilic copper enalcarbenoid has been disclosed here for the first time for its carbenoid reactivity. The synthetic utility of the transient Cu-enalcarbenoids has been demonstrated in the Cu-catalyzed direct synthesis of 1,7-disubstituted indoles from diazoenals and <em>N</em>-substituted pyrroles. In this reaction, Cu-enalcarbenoid served as a 4[C] biselectrophilic synthon whereas pyrrole served as a 2[C] bisnucleophilie leading to [4+2] benzannulation.</div></div>\",\"PeriodicalId\":1,\"journal\":{\"name\":\"Accounts of Chemical Research\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":16.4000,\"publicationDate\":\"2024-10-19\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Accounts of Chemical Research\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S004040392400426X\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Accounts of Chemical Research","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S004040392400426X","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

摘要

这里首次公开了一种具有高度亲电性的铜烯碳化合物，它具有类羰基化合物的反应活性。在铜催化下，重氮烯醛和 N-取代的吡咯直接合成 1,7-二取代吲哚的过程中，证明了瞬时铜烯碳烯酮的合成用途。在该反应中，Cu-烯碳化合物作为 4[C] 双亲电合成体，而吡咯作为 2[C] 双亲核体，导致 [4+2] 苯并反应。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

摘要图片

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

Copper-enalcarbenoids: Rapid access to 1,7-disubstituted indoles via [4+2] benzannulation between diazoenals and N-substituted pyrroles

A highly electrophilic copper enalcarbenoid has been disclosed here for the first time for its carbenoid reactivity. The synthetic utility of the transient Cu-enalcarbenoids has been demonstrated in the Cu-catalyzed direct synthesis of 1,7-disubstituted indoles from diazoenals and N-substituted pyrroles. In this reaction, Cu-enalcarbenoid served as a 4[C] biselectrophilic synthon whereas pyrrole served as a 2[C] bisnucleophilie leading to [4+2] benzannulation.

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

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.

期刊最新文献

Management of Cholesteatoma: Hearing Rehabilitation. Congenital Cholesteatoma. Evaluation of Cholesteatoma. Management of Cholesteatoma: Extension Beyond Middle Ear/Mastoid. Recidivism and Recurrence.