{"title":"Au(III)/TPPMS 催化水中失活 N-烷基苯胺的 Friedel-Crafts 苄基化反应。","authors":"Hidemasa Hikawa, Akane Fukuda, Kazuma Kondo, Taku Nakayama, Tomokatsu Enda, Shoko Kikkawa, Isao Azumaya","doi":"10.1039/d4ob01234h","DOIUrl":null,"url":null,"abstract":"<p><p>The Friedel-Crafts reaction of electronically deactivated anilines including those with strong electron-withdrawing NO<sub>2</sub>, CN or CO<sub>2</sub>H groups is challenging due to the reduced electron density of the aromatic ring. Here, we demonstrate the Au(III)/TPPMS-catalyzed Friedel-Crafts benzylation of deactivated anilines in water. This reaction exhibits operational simplicity and a broad substrate scope with high regioselectivity, enabling rapid access to 2-benzylanilines.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Au(III)/TPPMS-catalyzed Friedel-Crafts benzylation of deactivated <i>N</i>-alkylanilines in water.\",\"authors\":\"Hidemasa Hikawa, Akane Fukuda, Kazuma Kondo, Taku Nakayama, Tomokatsu Enda, Shoko Kikkawa, Isao Azumaya\",\"doi\":\"10.1039/d4ob01234h\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>The Friedel-Crafts reaction of electronically deactivated anilines including those with strong electron-withdrawing NO<sub>2</sub>, CN or CO<sub>2</sub>H groups is challenging due to the reduced electron density of the aromatic ring. Here, we demonstrate the Au(III)/TPPMS-catalyzed Friedel-Crafts benzylation of deactivated anilines in water. This reaction exhibits operational simplicity and a broad substrate scope with high regioselectivity, enabling rapid access to 2-benzylanilines.</p>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.9000,\"publicationDate\":\"2024-09-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d4ob01234h\",\"RegionNum\":3,\"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":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4ob01234h","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Au(III)/TPPMS-catalyzed Friedel-Crafts benzylation of deactivated N-alkylanilines in water.
The Friedel-Crafts reaction of electronically deactivated anilines including those with strong electron-withdrawing NO2, CN or CO2H groups is challenging due to the reduced electron density of the aromatic ring. Here, we demonstrate the Au(III)/TPPMS-catalyzed Friedel-Crafts benzylation of deactivated anilines in water. This reaction exhibits operational simplicity and a broad substrate scope with high regioselectivity, enabling rapid access to 2-benzylanilines.