{"title":"1,3‐Iodoesterification of 2‐Substituted Indoles via Csp2–H/Csp3–H Retained Dual Functionalization Using Hypervalent Iodine(III)","authors":"Hiroko Wasaki, Katsuhiko Moriyama","doi":"10.1002/adsc.202401496","DOIUrl":null,"url":null,"abstract":"A 1,3‐iodoesterification of 2‐substituted indoles with trihaloacetic acid, iodination reagent, and hypervalent iodine(III) compound was developed as an acid‐promoted C<sub>sp2</sub>–H/C<sub>sp3</sub>–H dual functionalization reaction to furnish 3‐iodo‐2‐trihaloacetoxymethyl indoles. The one‐pot 1,3‐iodoesterification/hydrolysis of the trihaloester group provided 3‐iodo‐2‐pivaloylmethyl indoles via the rearrangement of the pivaloyl group. The reaction proceeded through a trihaloacetic acid‐assisted electrophilic activation of the iodination reagent after the formation of an indolyl(mesityl)iodonium trihaloacetate.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"1 1","pages":""},"PeriodicalIF":4.4000,"publicationDate":"2025-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202401496","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
A 1,3‐iodoesterification of 2‐substituted indoles with trihaloacetic acid, iodination reagent, and hypervalent iodine(III) compound was developed as an acid‐promoted C<sub>sp2</sub>–H/C<sub>sp3</sub>–H dual functionalization reaction to furnish 3‐iodo‐2‐trihaloacetoxymethyl indoles. The one‐pot 1,3‐iodoesterification/hydrolysis of the trihaloester group provided 3‐iodo‐2‐pivaloylmethyl indoles via the rearrangement of the pivaloyl group. The reaction proceeded through a trihaloacetic acid‐assisted electrophilic activation of the iodination reagent after the formation of an indolyl(mesityl)iodonium trihaloacetate.
期刊介绍:
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
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