{"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":"<div><div>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(<span>iii</span>)/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.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"22 38","pages":"Pages 7874-7879"},"PeriodicalIF":2.7000,"publicationDate":"2024-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/ob/d4ob01234h?page=search","citationCount":"0","resultStr":"{\"title\":\"Au(iii)/TPPMS-catalyzed Friedel–Crafts benzylation of deactivated N-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\":\"<div><div>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(<span>iii</span>)/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.</div></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\"22 38\",\"pages\":\"Pages 7874-7879\"},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2024-10-02\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://pubs.rsc.org/en/content/articlepdf/2024/ob/d4ob01234h?page=search\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1477052024007869\",\"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://www.sciencedirect.com/org/science/article/pii/S1477052024007869","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.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.