• 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

一种用于钯催化芳基卤化物与硫醇偶联反应的通用且寿命长的催化剂。

A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols.

作者信息

Fernández-Rodríguez Manuel A, Shen Qilong, Hartwig John F

机构信息

Department of Chemistry, Yale University, PO Box 208107 New Haven, CT 06520-8107, USA.

出版信息

J Am Chem Soc. 2006 Feb 22;128(7):2180-1. doi: 10.1021/ja0580340.

DOI:10.1021/ja0580340
PMID:16478149
Abstract

A general catalytic system for the coupling of aryl halides and sulfonates with thiols based on the use of the CyPF-t-Bu ligand (1) is reported. The reactions catalyzed by complexes of 1 occur in excellent yields with broad scope and exhibit extraordinary turnover numbers and high tolerance of functional groups. Turnover numbers usually exceed those of previous catalysts by 2 or 3 orders of magnitude. In addition, the reactions of aryl tosylates with alkane thiols to form aryl sulfides are reported for the first time. Finally, the synthesis of a diarylsulfide from two bromoarenes was accomplished using a hydrogen sulfide surrogate.

摘要

报道了一种基于使用CyPF-t-Bu配体(1)的用于芳基卤化物和磺酸盐与硫醇偶联的通用催化体系。由1的配合物催化的反应产率优异、范围广泛,具有极高的周转数和对官能团的高耐受性。周转数通常比以前的催化剂高出2或3个数量级。此外,首次报道了芳基甲苯磺酸盐与链烷硫醇反应形成芳基硫醚。最后,使用硫化氢替代物由两种溴代芳烃合成了二芳基硫醚。

相似文献

1
A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols.一种用于钯催化芳基卤化物与硫醇偶联反应的通用且寿命长的催化剂。
J Am Chem Soc. 2006 Feb 22;128(7):2180-1. doi: 10.1021/ja0580340.
2
Highly efficient and functional-group-tolerant catalysts for the palladium-catalyzed coupling of aryl chlorides with thiols.用于钯催化芳基氯与硫醇偶联反应的高效且官能团耐受性良好的催化剂。
Chemistry. 2006 Oct 16;12(30):7782-96. doi: 10.1002/chem.200600949.
3
Indium-catalyzed C-S cross-coupling of aryl halides with thiols.铟催化芳基卤化物与硫醇的C-S交叉偶联反应。
J Org Chem. 2009 Apr 17;74(8):3189-91. doi: 10.1021/jo802731j.
4
Nano indium oxide as a recyclable catalyst for C-S cross-coupling of thiols with aryl halides under ligand free conditions.纳米氧化铟作为一种可循环使用的催化剂,用于在无配体条件下硫醇与芳基卤化物的C-S交叉偶联反应。
Org Lett. 2009 Apr 16;11(8):1697-700. doi: 10.1021/ol900009a.
5
The development of efficient catalysts for palladium-catalyzed coupling reactions of aryl halides.用于芳基卤化物钯催化偶联反应的高效催化剂的开发。
Chem Commun (Camb). 2005 Jan 28(4):431-40. doi: 10.1039/b410937f. Epub 2004 Dec 20.
6
Reevaluation of the mechanism of the amination of aryl halides catalyzed by BINAP-ligated palladium complexes.对BINAP连接的钯配合物催化芳基卤化物胺化反应机理的重新评估。
J Am Chem Soc. 2006 Mar 22;128(11):3584-91. doi: 10.1021/ja045533c.
7
A general and efficient catalyst for palladium-catalyzed C-O coupling reactions of aryl halides with primary alcohols.一种通用且高效的催化剂,用于钯催化芳基卤化物与伯醇的 C-O 偶联反应。
J Am Chem Soc. 2010 Aug 25;132(33):11592-8. doi: 10.1021/ja103248d.
8
Resting state and elementary steps of the coupling of aryl halides with thiols catalyzed by alkylbisphosphine complexes of palladium.钯烷基双膦配合物催化芳基卤化物与硫醇偶联反应的基态和基本步骤。
J Am Chem Soc. 2009 Jun 10;131(22):7858-68. doi: 10.1021/ja901793w.
9
A general, efficient, and functional-group-tolerant catalyst system for the palladium-catalyzed thioetherification of aryl bromides and iodides.一种用于钯催化芳基溴化物和碘化物硫醚化反应的通用、高效且官能团耐受性良好的催化剂体系。
J Org Chem. 2009 Feb 20;74(4):1663-72. doi: 10.1021/jo802594d.
10
Palladium-catalyzed homocoupling and cross-coupling reactions of aryl halides in poly(ethylene glycol).钯催化的芳基卤化物在聚乙二醇中的均偶联和交叉偶联反应
J Org Chem. 2006 Feb 3;71(3):1284-7. doi: 10.1021/jo052300a.

引用本文的文献

1
Metal-catalyzed methylthiolation of chloroarenes and diverse aryl electrophiles.金属催化氯代芳烃和多种芳基亲电试剂的甲硫基化反应。
Chem Sci. 2025 May 22. doi: 10.1039/d5sc01428j.
2
C(sp)-heteroatom bond formation by iron-catalyzed soft couplings.铁催化的温和偶联反应形成C(sp)-杂原子键。
Commun Chem. 2025 Mar 8;8(1):73. doi: 10.1038/s42004-025-01478-2.
3
Cross-Electrophile Coupling of Benzyl Halides and Disulfides Catalyzed by Iron.铁催化苄基卤化物与二硫化物的交叉亲电偶联反应
J Am Chem Soc. 2024 Feb 21;146(7):4903-4912. doi: 10.1021/jacs.3c13984. Epub 2024 Feb 12.
4
Visible-Light-Promoted C-S Cross-Coupling Reaction for Synthesis of Aromatic Thioethers.可见光促进的C-S交叉偶联反应合成芳香硫醚
Organic Synth. 2023;100:234-247. doi: 10.15227/orgsyn.100.0234. Epub 2023 Jun 15.
5
Silver Natural Asphalt Sulfonate (NA-SOAg): Fabrication and Utilization as a New Heterogeneous, Carbonaceous, and Retrievable Nanocatalyst for C(sp)- ( = C, S, and Se) Bond Formation.天然沥青银磺酸盐(NA-SOAg):作为一种用于形成C(sp)-(=C、S和Se)键的新型多相、含碳且可回收纳米催化剂的制备与应用
ACS Omega. 2023 Sep 22;8(39):36152-36161. doi: 10.1021/acsomega.3c04447. eCollection 2023 Oct 3.
6
Sulfoximine Assisted C-H Activation and Annulation via Vinylene Transfer: Access to Unsubstituted Benzothiazines.亚砜亚胺辅助的 C-H 活化和炔烃转移环化反应:构建未取代的苯并噻嗪。
Molecules. 2023 Jun 27;28(13):5014. doi: 10.3390/molecules28135014.
7
Dimsyl Anion Enables Visible-Light-Promoted Charge Transfer in Cross-Coupling Reactions of Aryl Halides.二甲基亚砜阴离子使芳基卤化物交叉偶联反应中的可见光促进电荷转移成为可能。
Adv Synth Catal. 2022 Jan 18;364(2):420-425. doi: 10.1002/adsc.202101052. Epub 2021 Oct 15.
8
Efficient Construction of Symmetrical Diaryl Sulfides via a Supported Pd Nanocatalyst-Catalyzed C-S Coupling Reaction.通过负载型钯纳米催化剂催化的 C-S 偶联反应高效构建对称二芳基硫醚。
Int J Mol Sci. 2022 Dec 6;23(23):15360. doi: 10.3390/ijms232315360.
9
Effective Formation of New C(sp )-S Bonds via Photoactivation of Alkylamine-based Electron Donor-Acceptor Complexes.通过基于供电子-受电子体复合物的光活化作用来有效形成新的 C(sp )-S 键。
Chemistry. 2023 Jan 27;29(6):e202203353. doi: 10.1002/chem.202203353. Epub 2022 Dec 5.
10
Forging C-S Bonds Through Decarbonylation: New Perspectives for the Synthesis of Privileged Aryl Sulfides.通过脱羰基作用形成碳-硫键:合成特殊芳基硫醚的新视角
ChemCatChem. 2021 Dec 7;13(23):4878-4881. doi: 10.1002/cctc.202101206. Epub 2021 Sep 25.