{"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}
引用次数: 0
Abstract
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.