{"title":"通过与1-(2-羟基苯基)-丙炔醇的一锅两步反应,i2诱导无金属C(sp2) - h功能化吲哚:获得3-(苯并呋喃-3-基)- 1h -吲哚","authors":"Yang Zhu, Guisheng Deng","doi":"10.1021/acs.joc.4c03109","DOIUrl":null,"url":null,"abstract":"The I<sub>2</sub>-catalyzed reaction of 1-(2-hydroxyphenyl)-propargyl alcohols with indoles and subsequent treatment with K<sub>2</sub>CO<sub>3</sub> provided (benzofuran-3-yl)-1<i>H</i>-indoles in good to excellent yields with high regioselectivity. This one-pot and two-step strategy proved to be suitable for a wide range of substrates except for aliphatic alkynyl alcohols as well as the indoles bearing <i>N</i>-protected groups such as the Ts group possessing strong electron-withdrawing feature. The reaction procedure involved a cross-coupling and the construction of a benzofuran framework via 5-<i>exo-dig</i> cyclization.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"33 1","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"I2-Induced Metal-Free C(sp2)–H Functionalization of Indoles via One-Pot and Two-Step Reaction with 1-(2-Hydroxyphenyl)-propargyl Alcohols: Access to 3-(Benzofuran-3-yl)-1H-indoles\",\"authors\":\"Yang Zhu, Guisheng Deng\",\"doi\":\"10.1021/acs.joc.4c03109\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"The I<sub>2</sub>-catalyzed reaction of 1-(2-hydroxyphenyl)-propargyl alcohols with indoles and subsequent treatment with K<sub>2</sub>CO<sub>3</sub> provided (benzofuran-3-yl)-1<i>H</i>-indoles in good to excellent yields with high regioselectivity. This one-pot and two-step strategy proved to be suitable for a wide range of substrates except for aliphatic alkynyl alcohols as well as the indoles bearing <i>N</i>-protected groups such as the Ts group possessing strong electron-withdrawing feature. The reaction procedure involved a cross-coupling and the construction of a benzofuran framework via 5-<i>exo-dig</i> cyclization.\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\"33 1\",\"pages\":\"\"},\"PeriodicalIF\":3.6000,\"publicationDate\":\"2025-04-03\",\"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.4c03109\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c03109","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
I2-Induced Metal-Free C(sp2)–H Functionalization of Indoles via One-Pot and Two-Step Reaction with 1-(2-Hydroxyphenyl)-propargyl Alcohols: Access to 3-(Benzofuran-3-yl)-1H-indoles
The I2-catalyzed reaction of 1-(2-hydroxyphenyl)-propargyl alcohols with indoles and subsequent treatment with K2CO3 provided (benzofuran-3-yl)-1H-indoles in good to excellent yields with high regioselectivity. This one-pot and two-step strategy proved to be suitable for a wide range of substrates except for aliphatic alkynyl alcohols as well as the indoles bearing N-protected groups such as the Ts group possessing strong electron-withdrawing feature. The reaction procedure involved a cross-coupling and the construction of a benzofuran framework via 5-exo-dig cyclization.
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.