{"title":"Transition-metal-free tandem cyclization by radical NHC catalysis: Rapid access to indolo[2,1‑a]isoquinolines","authors":"","doi":"10.1016/j.tetlet.2024.155319","DOIUrl":null,"url":null,"abstract":"<div><div>A diverse array of functionalized indolo[2,1-<em>a</em>]isoquinolines are constructed through an NHC-catalyzed transition-metal-, and oxidant-free radical tandem cyclization from readily accessible 2-aryl N-methacryloyl indoles and α-bromo esters. This redox-neutral protocol exhibits a wide substrate scope, excellent functional group tolerance, and can be scaled up to 2.0 mmol with parallel efficiency. Mechanistic studies suggest that a single electron transfer radical process is likely involved.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5000,"publicationDate":"2024-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924004143","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A diverse array of functionalized indolo[2,1-a]isoquinolines are constructed through an NHC-catalyzed transition-metal-, and oxidant-free radical tandem cyclization from readily accessible 2-aryl N-methacryloyl indoles and α-bromo esters. This redox-neutral protocol exhibits a wide substrate scope, excellent functional group tolerance, and can be scaled up to 2.0 mmol with parallel efficiency. Mechanistic studies suggest that a single electron transfer radical process is likely involved.
期刊介绍:
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.