{"title":"B(C6F5)3-Catalyzed Reductive Deoxygenation of Isatins for Indole Synthesis","authors":"Seung Deok Son, Hoe Young Choi, Haye Min Ko","doi":"10.1021/acs.joc.5c00345","DOIUrl":null,"url":null,"abstract":"An efficient method for reductive deoxygenation of isatin derivatives using catalyst B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> and methylphenylsilane is described. This reaction proceeds rapidly under mild conditions, and the protocol provides a broad substrate scope. Notably, while general synthetic methods utilizing a combination of B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> and hydrosilanes smoothly reduce indoles to generate indolines, the present strategy represents the first reductive deoxygenation reaction for the formation of indoles without further reduction.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"33 1","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2025-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.5c00345","RegionNum":2,"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
Abstract
An efficient method for reductive deoxygenation of isatin derivatives using catalyst B(C6F5)3 and methylphenylsilane is described. This reaction proceeds rapidly under mild conditions, and the protocol provides a broad substrate scope. Notably, while general synthetic methods utilizing a combination of B(C6F5)3 and hydrosilanes smoothly reduce indoles to generate indolines, the present strategy represents the first reductive deoxygenation reaction for the formation of indoles without further reduction.
期刊介绍:
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.