• 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

一种在温和条件下用于芳基氯和芳基溴的Heck反应的多功能催化剂。

A versatile catalyst for Heck reactions of aryl chlorides and aryl bromides under mild conditions.

作者信息

Littke A F, Fu G C

机构信息

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

出版信息

J Am Chem Soc. 2001 Jul 25;123(29):6989-7000. doi: 10.1021/ja010988c.

DOI:10.1021/ja010988c
PMID:11459477
Abstract

In the presence of Cy2NMe, Pd/P(t-Bu)3 serves as an exceptionally mild and versatile catalyst for Heck reactions of aryl chlorides and bromides. A sterically and electronically diverse array of aryl bromides, as well as activated aryl chlorides, couple with a range of mono- and disubstituted olefins at room temperature, furnishing the arylated product with high E/Z stereoselection. The corresponding reactions of a broad spectrum of electron-neutral and electron-rich aryl chlorides proceed at elevated temperature, also with high selectivity. In terms of scope and mildness, Pd/P(t-Bu)3/Cy2NMe represents an advance over previously reported catalysts for these Heck coupling processes.

摘要

在Cy2NMe存在的情况下,Pd/P(t-Bu)3作为一种极其温和且通用的催化剂,用于芳基氯和芳基溴的Heck反应。一系列空间和电子性质各异的芳基溴以及活性芳基氯,在室温下能与多种单取代和双取代烯烃发生偶联反应,以高E/Z立体选择性生成芳基化产物。多种电子中性和富电子芳基氯的相应反应在高温下也能进行,且同样具有高选择性。就反应范围和温和性而言,Pd/P(t-Bu)3/Cy2NMe相较于此前报道的用于这些Heck偶联反应的催化剂有了进步。

相似文献

1
A versatile catalyst for Heck reactions of aryl chlorides and aryl bromides under mild conditions.一种在温和条件下用于芳基氯和芳基溴的Heck反应的多功能催化剂。
J Am Chem Soc. 2001 Jul 25;123(29):6989-7000. doi: 10.1021/ja010988c.
2
Pd/P(t-Bu)(3): a mild and general catalyst for Stille reactions of aryl chlorides and aryl bromides.钯/三叔丁基膦:一种用于芳基氯和芳基溴的施蒂勒反应的温和通用催化剂。
J Am Chem Soc. 2002 Jun 5;124(22):6343-8. doi: 10.1021/ja020012f.
3
A surprisingly mild and versatile method for palladium-catalyzed Suzuki cross-couplings of aryl chlorides in the presence of a triarylphosphine.一种在三芳基膦存在下用于钯催化芳基氯进行铃木交叉偶联反应的出人意料地温和且通用的方法。
Chem Commun (Camb). 2001 Dec 7(23):2408-9.
4
From α-arylation of olefins to acylation with aldehydes: a journey in regiocontrol of the Heck reaction.从烯烃的α-芳基化到与醛的酰化:Heck 反应区域控制的历程。
Acc Chem Res. 2011 Aug 16;44(8):614-26. doi: 10.1021/ar200053d. Epub 2011 May 25.
5
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.
6
Arylalkene synthesis via decarboxylative cross-coupling of alkenyl halides.芳基烯烃的合成通过烯基卤化物的脱羧交叉偶联反应。
Org Lett. 2014 May 16;16(10):2664-7. doi: 10.1021/ol500876x. Epub 2014 May 6.
7
An improved palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides.改进的钯催化芳基和乙烯基三氟甲磺酸酯转化为溴化物和氯化物。
Org Lett. 2011 Sep 16;13(18):4974-6. doi: 10.1021/ol202098h. Epub 2011 Aug 24.
8
Bulky alkylphosphines with neopentyl substituents as ligands in the amination of aryl bromides and chlorides.带有新戊基取代基的大体积烷基膦作为芳基溴化物和氯化物胺化反应中的配体。
J Org Chem. 2006 Jul 7;71(14):5117-25. doi: 10.1021/jo060303x.
9
Palladium-catalyzed coupling reactions of aryl chlorides.芳基氯化物的钯催化偶联反应。
Angew Chem Int Ed Engl. 2002 Nov 15;41(22):4176-211. doi: 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U.
10
Investigations into the Pd-catalysed cross-coupling of phenylacetylene with aryl chlorides: simple one-pot procedure and the effect of ZnCl2 co-catalysis.钯催化苯乙炔与芳基氯的交叉偶联反应研究:简单的一锅法及氯化锌共催化的影响
Chem Commun (Camb). 2002 Apr 21(8):818-9. doi: 10.1039/b200453b.

引用本文的文献

1
Ligand Type Guided Keto-Arylation Enables Modular Total Synthesis of Polycyclic CBS Xanthones.配体类型导向的酮芳基化反应实现多环CBS呫吨酮的模块化全合成。
Angew Chem Int Ed Engl. 2025 Sep 8;64(37):e202513532. doi: 10.1002/anie.202513532. Epub 2025 Jul 22.
2
Xanthopinacol Boronate: A Robust, Photochemically Assembled and Cleavable Boronic Ester for Orthogonal Chemistry.黄嘌呤硼酸酯:一种用于正交化学的坚固、光化学组装且可裂解的硼酸酯。
Angew Chem Int Ed Engl. 2025 Jul 7;64(28):e202507571. doi: 10.1002/anie.202507571. Epub 2025 May 13.
3
Carborane-based BODIPY dyes: synthesis, structural analysis, photophysics and applications.
基于碳硼烷的氟硼二吡咯染料:合成、结构分析、光物理性质及应用
Front Chem. 2024 Nov 5;12:1485301. doi: 10.3389/fchem.2024.1485301. eCollection 2024.
4
Formate-Mediated Reductive Cross-Coupling of Vinyl Halides and Aryl Iodides: -Substitution via Palladium(I) Catalysis.卤代乙烯和芳基碘化物的甲酸介导还原交叉偶联:通过钯(I)催化的α-取代反应
Org Lett. 2024 Aug 23;26(33):7055-7059. doi: 10.1021/acs.orglett.4c02642. Epub 2024 Aug 12.
5
A green Heck reaction protocol towards trisubstituted alkenes, versatile pharmaceutical intermediates.一种用于制备三取代烯烃(通用药物中间体)的绿色Heck反应方案。
Front Chem. 2024 Jul 10;12:1431382. doi: 10.3389/fchem.2024.1431382. eCollection 2024.
6
Assisted Tandem Pd Catalysis Enables Regiodivergent Heck Arylation of Transiently Generated Substituted Enol Ethers.辅助串联钯催化实现瞬态生成的取代烯醇醚的区域发散性 Heck 芳基化反应。
JACS Au. 2023 Jan 12;3(1):261-274. doi: 10.1021/jacsau.2c00645. eCollection 2023 Jan 23.
7
A cyanide-catalyzed imino-Stetter reaction enables the concise total syntheses of rucaparib.氰化物催化的亚氨基-施泰特反应实现了芦卡帕尼的简洁全合成。
RSC Adv. 2022 Aug 1;12(33):21172-21180. doi: 10.1039/d2ra03619c. eCollection 2022 Jul 21.
8
Programmed Polyene Cyclization Enabled by Chromophore Disruption.受发色团破坏影响的聚轮烯类化合物的程序性环化。
J Am Chem Soc. 2022 Apr 13;144(14):6193-6199. doi: 10.1021/jacs.2c02144. Epub 2022 Apr 4.
9
Halogen-Bridged Methylnaphthyl Palladium Dimers as Versatile Catalyst Precursors in Coupling Reactions.卤代桥连甲基萘基钯二聚体作为偶联反应中通用的催化剂前体
Angew Chem Int Ed Engl. 2021 Nov 15;60(47):25151-25160. doi: 10.1002/anie.202110450. Epub 2021 Oct 15.
10
Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis.通过膦钯催化实现呋喃天然产物的统一方法。
Angew Chem Int Ed Engl. 2021 Apr 12;60(16):8874-8881. doi: 10.1002/anie.202015232. Epub 2021 Mar 8.