{"title":"Aryne Generation from o-Triazenylarylboronic Acids Induced by 1,2-Diols and 4-Nitrophenol","authors":"Motoki Ito, Hiroki Yomo, Kazuhiro Higuchi, Shigeo Sugiyama","doi":"10.1021/acs.joc.4c02946","DOIUrl":null,"url":null,"abstract":"Arynes are important synthetic intermediates that are usually generated under alkaline conditions. We developed a method for generating arynes using two hydroxy compounds as activators. <i>o</i>-Triazenylarylboronic acids generate (hetero)arynes when activated by a combination of ethylene glycol, pinacol, and <i>p</i>-nitrophenol; these arynes then react with a range of arynophiles under slightly acidic conditions that complement the conventional basic conditions with unique chemoselectivities observed even in the presence of excess hydroxy compounds.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"28 1","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-01-30","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.4c02946","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
Arynes are important synthetic intermediates that are usually generated under alkaline conditions. We developed a method for generating arynes using two hydroxy compounds as activators. o-Triazenylarylboronic acids generate (hetero)arynes when activated by a combination of ethylene glycol, pinacol, and p-nitrophenol; these arynes then react with a range of arynophiles under slightly acidic conditions that complement the conventional basic conditions with unique chemoselectivities observed even in the presence of excess hydroxy compounds.
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.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
