Nickel-Catalyzed Atroposelective Cross-Electrophile Coupling of Aryl Halides: A General and Practical Route to Diverse MOP-Type Ligands

IF 14.4 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Journal of the American Chemical Society Pub Date : 2024-05-23 DOI:10.1021/jacs.4c04608
Raphael S. Kim, Lebogang O. Kgoadi, Jacob C. Hayes, Derek P. Rainboth, Catherine M. Mudd, Glenn P. A. Yap and Donald A. Watson*, 
{"title":"Nickel-Catalyzed Atroposelective Cross-Electrophile Coupling of Aryl Halides: A General and Practical Route to Diverse MOP-Type Ligands","authors":"Raphael S. Kim,&nbsp;Lebogang O. Kgoadi,&nbsp;Jacob C. Hayes,&nbsp;Derek P. Rainboth,&nbsp;Catherine M. Mudd,&nbsp;Glenn P. A. Yap and Donald A. Watson*,&nbsp;","doi":"10.1021/jacs.4c04608","DOIUrl":null,"url":null,"abstract":"<p >We report a highly cross- and atroposelective coupling between <i>ortho</i>-(chloro)arylphosphine oxides and <i>ortho</i>-(bromo)aryl ethers. This previously unknown asymmetric nickel-catalyzed reaction offers a direct route to highly enantioenriched axially chiral biaryl monophosphine oxides that are difficult to access by other means. These products can be readily reduced to generate chiral MOP-type ligands bearing complex skeletal backbones. The utility of these chiral ligands in asymmetric catalysis is also demonstrated.</p>","PeriodicalId":49,"journal":{"name":"Journal of the American Chemical Society","volume":null,"pages":null},"PeriodicalIF":14.4000,"publicationDate":"2024-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the American Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/jacs.4c04608","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0

Abstract

We report a highly cross- and atroposelective coupling between ortho-(chloro)arylphosphine oxides and ortho-(bromo)aryl ethers. This previously unknown asymmetric nickel-catalyzed reaction offers a direct route to highly enantioenriched axially chiral biaryl monophosphine oxides that are difficult to access by other means. These products can be readily reduced to generate chiral MOP-type ligands bearing complex skeletal backbones. The utility of these chiral ligands in asymmetric catalysis is also demonstrated.

Abstract Image

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
镍催化芳基卤化物的逆选择性跨亲电偶合:通向多种 MOP 型配体的通用实用途径。
我们报告了正(氯)芳基膦氧化物与正(溴)芳基醚之间的高度交叉和反向选择性偶联。这种以前未知的不对称镍催化反应为获得其他方法难以获得的高对映体轴向手性双芳基单膦氧化物提供了一条直接途径。这些产物很容易被还原生成具有复杂骨架的手性 MOP 型配体。这些手性配体在不对称催化中的用途也得到了证实。
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 去求助
来源期刊
CiteScore
24.40
自引率
6.00%
发文量
2398
审稿时长
1.6 months
期刊介绍: The flagship journal of the American Chemical Society, known as the Journal of the American Chemical Society (JACS), has been a prestigious publication since its establishment in 1879. It holds a preeminent position in the field of chemistry and related interdisciplinary sciences. JACS is committed to disseminating cutting-edge research papers, covering a wide range of topics, and encompasses approximately 19,000 pages of Articles, Communications, and Perspectives annually. With a weekly publication frequency, JACS plays a vital role in advancing the field of chemistry by providing essential research.
期刊最新文献
A Bioinspired Nonheme FeIII-(O22-)-CuII Complex with an St = 1 Ground State. Catalyst Editing via Post-Synthetic Functionalization by Phosphonium Generation and Anion Exchange for Nickel-Catalyzed Ethylene/Acrylate Copolymerization. Diverse Synthesis of C-Glycosides by Stereoselective Ni-Catalyzed Carboboration of Glycals. Elucidating the Transport of Electrons and Molecules in a Solid Electrolyte Interphase Close to Battery Operation Potentials Using a Four-Electrode-Based Generator-Collector Setup. Interrogation of Oxidative Pulsed Methods for the Stabilization of Copper Electrodes for CO2 Electrolysis.
×
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
现在去查看 取消
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 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 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1