A General Pd-Catalyzed C2–H Arylation of Benzoxazoles with Highly Sterically Congested Aryl Chlorides Enabled by a Fittingly Tuned Ligand

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC
Weijian Song, Man Ho Tse, Yu Kiu Lau, Chi Wai Cheung*, Pui Ying Choy* and Fuk Yee Kwong*, 
{"title":"A General Pd-Catalyzed C2–H Arylation of Benzoxazoles with Highly Sterically Congested Aryl Chlorides Enabled by a Fittingly Tuned Ligand","authors":"Weijian Song,&nbsp;Man Ho Tse,&nbsp;Yu Kiu Lau,&nbsp;Chi Wai Cheung*,&nbsp;Pui Ying Choy* and Fuk Yee Kwong*,&nbsp;","doi":"10.1021/acs.orglett.4c0411710.1021/acs.orglett.4c04117","DOIUrl":null,"url":null,"abstract":"<p >The benzoxazole core, featuring a sterically congested 2,6-disubstituted aryl fragment at the C2 position, exhibits exclusive three-dimensional structures that are essential for particular applications in material science and pharmaceutical development. Despite their importance, the synthesis of these compounds has posed challenges with an efficient preparation strategy still lacking. In this study, we introduced a new indolylphosphine ligand, <b>PCy</b><sub><b>2</b></sub><b>-Man-phos</b>, specifically designed to facilitate the C2–H arylation of benzoxazoles with sterically hindered aryl chlorides in general. The excellent functional group compatibility and rich arene substituted pattern enable the creation of highly decorated and sterically demanding 2-arylbenzoxazole frameworks, showing significant potential for diverse synthetic applications.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 50","pages":"10958–10963 10958–10963"},"PeriodicalIF":5.0000,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.4c04117","RegionNum":1,"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 benzoxazole core, featuring a sterically congested 2,6-disubstituted aryl fragment at the C2 position, exhibits exclusive three-dimensional structures that are essential for particular applications in material science and pharmaceutical development. Despite their importance, the synthesis of these compounds has posed challenges with an efficient preparation strategy still lacking. In this study, we introduced a new indolylphosphine ligand, PCy2-Man-phos, specifically designed to facilitate the C2–H arylation of benzoxazoles with sterically hindered aryl chlorides in general. The excellent functional group compatibility and rich arene substituted pattern enable the creation of highly decorated and sterically demanding 2-arylbenzoxazole frameworks, showing significant potential for diverse synthetic applications.

Abstract Image

适当调节配体使苯并恶唑与高度空间拥塞芳酰氯的一般pd催化的C2-H芳化反应成为可能
苯并恶唑核心,在C2位置具有一个空间拥挤的2,6-二取代芳基片段,具有独特的三维结构,在材料科学和药物开发中的特殊应用是必不可少的。尽管这些化合物具有重要意义,但由于缺乏有效的制备策略,它们的合成面临挑战。在这项研究中,我们引入了一种新的吲哚膦配体PCy2-Man-phos,专门用于促进苯并恶唑与空间位阻芳酰氯的C2-H芳化。优异的官能团相容性和丰富的芳烃取代模式使得2-芳基苯并恶唑结构具有很高的装饰性和立体要求,具有广泛的合成应用潜力。
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
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
×
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:604180095
Book学术官方微信