• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

新型空气稳定的平面手性二茂铁基单膦配体:芳基氯化物和溴化物的铃木交叉偶联反应

New air-stable planar chiral ferrocenyl monophosphine ligands: Suzuki cross-coupling of aryl chlorides and bromides.

作者信息

Jensen Jakob F, Johannsen Mogens

机构信息

Department of Chemistry, Technical University of Denmark, Building 201, Dk-2800 Kgs. Lyngby, Denmark.

出版信息

Org Lett. 2003 Aug 21;5(17):3025-8. doi: 10.1021/ol034943n.

DOI:10.1021/ol034943n
PMID:12916972
Abstract

[reaction: see text] A novel class of planar chiral electron-rich monophosphine ligands has been developed. The modular design allows a short and efficient synthesis of an array of aryl-ferrocenyl derivatives carrying the donating bis(dicyclohexyl)phosphino moiety. These new ligands have successfully been applied in the palladium-catalyzed Suzuki cross-coupling of activated as well as nonactivated aryl chlorides at room temperature. The asymmetric coupling of an aryl bromide and an aryl boronic acid was also tested, giving ees up to 54%.

摘要

[反应:见正文] 已开发出一类新型的平面手性富电子单膦配体。模块化设计使得能够短而高效地合成一系列带有供电子双(二环己基)膦基部分的芳基 - 二茂铁基衍生物。这些新配体已成功应用于钯催化的室温下活性和非活性芳基氯化物的铃木交叉偶联反应。还测试了芳基溴化物与芳基硼酸的不对称偶联反应,对映体过量率高达54%。

相似文献

1
New air-stable planar chiral ferrocenyl monophosphine ligands: Suzuki cross-coupling of aryl chlorides and bromides.新型空气稳定的平面手性二茂铁基单膦配体:芳基氯化物和溴化物的铃木交叉偶联反应
Org Lett. 2003 Aug 21;5(17):3025-8. doi: 10.1021/ol034943n.
2
Ferrocenyl monophosphine ligands: synthesis and applications in the Suzuki-Miyaura coupling of aryl chlorides.二茂铁基单膦配体:芳基氯代物在铃木-宫浦偶联反应中的合成及应用
J Org Chem. 2004 Oct 29;69(22):7779-82. doi: 10.1021/jo048963u.
3
Modular approach to novel chiral aryl-ferrocenyl phosphines by Suzuki cross-coupling.通过铃木交叉偶联法合成新型手性芳基 - 二茂铁基膦的模块化方法。
J Org Chem. 2003 Feb 21;68(4):1258-65. doi: 10.1021/jo026250a.
4
Macromolecular effect: synthesis of a ferrocenylmethylphosphine-containing polymer as highly efficient ligands for room-temperature palladium(0)-catalyzed Suzuki cross-coupling reactions of aryl chlorides.大分子效应:含二茂铁基甲基膦聚合物的合成作为用于芳基氯室温钯(0)催化铃木交叉偶联反应的高效配体。
J Am Chem Soc. 2003 Mar 12;125(10):2856-7. doi: 10.1021/ja029021e.
5
Novel class of tertiary phosphine ligands based on a phospha-adamantane framework and use in the Suzuki cross-coupling reactions of aryl halides under mild conditions.基于磷金刚烷骨架的新型叔膦配体及其在温和条件下芳基卤化物的铃木交叉偶联反应中的应用。
Org Lett. 2003 Mar 20;5(6):953-5. doi: 10.1021/ol0341647.
6
Practical synthesis of new and highly efficient ligands for the Suzuki reaction of aryl chlorides.用于芳基氯代物铃木反应的新型高效配体的实用合成方法。
Chem Commun (Camb). 2004 Jan 7(1):38-9. doi: 10.1039/b311268n. Epub 2003 Nov 28.
7
Simple amine/Pd(OAc)(2)-catalyzed suzuki coupling reactions of aryl bromides under mild aerobic conditions.简单胺/醋酸钯(II)催化的芳基溴化物在温和有氧条件下的铃木偶联反应。
J Org Chem. 2004 Jun 25;69(13):4330-5. doi: 10.1021/jo040147z.
8
[2.2]Paracyclophane-based monophosphine ligand for palladium-catalyzed cross-coupling reactions of aryl chlorides.基于对三联苯的单膦配体在芳基氯的钯催化交叉偶联反应中的应用。
Org Biomol Chem. 2009 Aug 21;7(16):3236-42. doi: 10.1039/b906139h. Epub 2009 Jun 17.
9
Triazole-based monophosphine ligands for palladium-catalyzed cross-coupling reactions of aryl chlorides.用于钯催化芳基氯交叉偶联反应的基于三唑的单膦配体
J Org Chem. 2006 May 12;71(10):3928-34. doi: 10.1021/jo060321e.
10
Highly active palladium catalysts supported by bulky proazaphosphatrane ligands for Stille cross-coupling: coupling of aryl and vinyl chlorides, room temperature coupling of aryl bromides, coupling of aryl triflates, and synthesis of sterically hindered biaryls.用于Stille交叉偶联的由大位阻前氮磷杂环卡宾配体负载的高活性钯催化剂:芳基和乙烯基氯的偶联、芳基溴的室温偶联、芳基三氟甲磺酸酯的偶联以及位阻联芳基的合成。
J Am Chem Soc. 2004 Dec 22;126(50):16433-9. doi: 10.1021/ja0450096.

引用本文的文献

1
Palladium-Catalyzed Atroposelective Suzuki-Miyaura Coupling to Construct Axially Chiral Tetra-Substituted α-Boryl Styrenes.钯催化的对映选择性铃木-宫浦偶联反应构建轴向手性四取代α-硼基苯乙烯类化合物
Adv Sci (Weinh). 2024 Jun;11(24):e2309706. doi: 10.1002/advs.202309706. Epub 2024 Apr 11.
2
Pd-catalyzed asymmetric Suzuki-Miyaura coupling reactions for the synthesis of chiral biaryl compounds with a large steric substituent at the 2-position.钯催化的不对称铃木-宫浦偶联反应,用于合成在2-位带有大空间位阻取代基的手性联芳基化合物。
Beilstein J Org Chem. 2020 May 11;16:966-973. doi: 10.3762/bjoc.16.85. eCollection 2020.
3
Crystal structure of (2-acetyl-ferrocen-1-yl)boronic acid.
(2-乙酰基-二茂铁-1-基)硼酸的晶体结构
Acta Crystallogr E Crystallogr Commun. 2019 Jan 29;75(Pt 2):268-271. doi: 10.1107/S2056989019001178. eCollection 2019 Feb 1.
4
Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling.用于钯催化交叉偶联的膦基三唑配体
Organometallics. 2018 Nov 26;37(22):4224-4241. doi: 10.1021/acs.organomet.8b00539. Epub 2018 Oct 17.
5
Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki-Miyaura and Negishi Cross-Coupling Reactions for Tetra-Substituted Biaryl Synthesis.钯催化的不对称铃木-宫浦和根岸交叉偶联反应用于四取代联芳基合成的计算辅助机理研究与开发
ACS Catal. 2018 Nov 2;8(11):10190-10209. doi: 10.1021/acscatal.8b02509. Epub 2018 Sep 20.
6
Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.用于构建碳-碳键的有机金属试剂的对映选择性和对映特异性过渡金属催化交叉偶联反应。
Chem Rev. 2015 Sep 9;115(17):9587-652. doi: 10.1021/acs.chemrev.5b00162. Epub 2015 Aug 13.
7
Development of Chiral Bis-hydrazone Ligands for the Enantioselective Cross-Coupling Reactions of Aryldimethylsilanolates.用于芳基二甲基硅醇盐对映选择性交叉偶联反应的手性双腙配体的开发
J Org Chem. 2015 Jan 2;80(1):313-66. doi: 10.1021/jo502388r. Epub 2014 Dec 10.
8
Enantioselective synthesis of axially chiral biaryls by the Pd-catalyzed Suzuki-Miyaura reaction: substrate scope and quantum mechanical investigations.通过钯催化的 Suzuki-Miyaura 反应对轴手性联芳基的对映选择性合成:底物范围和量子力学研究。
J Am Chem Soc. 2010 Aug 18;132(32):11278-87. doi: 10.1021/ja104297g.
9
Biaryl phosphane ligands in palladium-catalyzed amination.钯催化胺化反应中的联芳基膦配体
Angew Chem Int Ed Engl. 2008;47(34):6338-61. doi: 10.1002/anie.200800497.