Rhodium-Catalyzed C–H Arylation of Indoles with Arylsilanes at Room Temperature

IF 3.3 2区 化学 Q1 CHEMISTRY, ORGANIC
Tingting Hou, Xin Wang, Deyu Wu, Xin Yang, Guang Li*, Heng Xu* and Yi Dong*, 
{"title":"Rhodium-Catalyzed C–H Arylation of Indoles with Arylsilanes at Room Temperature","authors":"Tingting Hou,&nbsp;Xin Wang,&nbsp;Deyu Wu,&nbsp;Xin Yang,&nbsp;Guang Li*,&nbsp;Heng Xu* and Yi Dong*,&nbsp;","doi":"10.1021/acs.joc.4c0154910.1021/acs.joc.4c01549","DOIUrl":null,"url":null,"abstract":"<p >The Cp*Rh-catalyzed C–H arylation of indoles with arylsilanes is developed. This C–H activation transformation allows for the Rh-catalyzed indole C<sub>2</sub> arylation to overcome the limitations of requiring strong directing group assistance and high-temperature conditions, achieving a room-temperature transformation driven by a weak directing group. Cp*Rh/MeOH catalytic media are considered a key factor enabling this transformation to occur under mild conditions, and experimental studies and theoretical calculations were performed to rationalize the reaction mechanisms and the influence of methanol as a solvent in promoting the reaction.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16406–16418 16406–16418"},"PeriodicalIF":3.3000,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.joc.4c01549","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

The Cp*Rh-catalyzed C–H arylation of indoles with arylsilanes is developed. This C–H activation transformation allows for the Rh-catalyzed indole C2 arylation to overcome the limitations of requiring strong directing group assistance and high-temperature conditions, achieving a room-temperature transformation driven by a weak directing group. Cp*Rh/MeOH catalytic media are considered a key factor enabling this transformation to occur under mild conditions, and experimental studies and theoretical calculations were performed to rationalize the reaction mechanisms and the influence of methanol as a solvent in promoting the reaction.

Abstract Image

室温下铑催化吲哚与芳基硅烷的 C-H 芳基化反应
我们开发了 Cp*Rh 催化吲哚与芳基硅烷的 C-H 芳基化反应。这种 C-H 活化转化使 Rh 催化的吲哚 C2 芳基化克服了需要强引导基辅助和高温条件的限制,实现了由弱引导基驱动的室温转化。Cp*Rh/MeOH 催化介质被认为是使这一转化在温和条件下发生的关键因素,实验研究和理论计算旨在合理解释反应机理以及甲醇作为溶剂对促进反应的影响。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
The Journal of Organic Chemistry
The Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: The 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.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信