• 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

钯(0)催化、铜(I)介导的环状硫代酰胺与烯基硼酸、有机锡烷和硅氧烷的偶联反应。

Palladium(0)-catalyzed, copper(i)-mediated coupling of cyclic thioamides with alkenylboronic acids, organostannanes, and siloxanes.

作者信息

Arshad Nuzhat, Hashim Jamshed, Kappe C Oliver

机构信息

Christian Doppler Laboratory for Microwave Chemistry (CDLMC) and Institute of Chemistry, Karl-Franzens-University Graz, Heinrichstrasse 28, A-8010 Graz, Austria.

出版信息

J Org Chem. 2009 Jul 17;74(14):5118-21. doi: 10.1021/jo900848s.

DOI:10.1021/jo900848s
PMID:19463003
Abstract

The Pd-catalyzed cross-coupling of cyclic thioamides and thioureas with alkenylboronic acids, vinyl- and (het)arylstannanes, and arylsiloxanes in the presence of stoichiometric amounts of a Cu(I) cofactor is described. The desulfitative C-C cross-coupling protocol of the Liebeskind-Srogl type is performed under neutral conditions and can be applied to a range of heterocyclic structures with embedded thioamide fragments. Employing controlled microwave irradiation at 100 degrees C utilizing either a single-mode reactor or a multimode parallel reaction platform, cross-couplings can generally be completed within 1-3 h and proceed in good yields.

摘要

描述了在化学计量的Cu(I)辅助因子存在下,钯催化环状硫代酰胺和硫脲与烯基硼酸、乙烯基和(杂)芳基锡烷以及芳基硅氧烷的交叉偶联反应。Liebeskind-Srogl型脱硫C-C交叉偶联反应在中性条件下进行,可应用于一系列含有硫代酰胺片段的杂环结构。利用单模反应器或多模平行反应平台在100℃下进行受控微波辐射,交叉偶联反应通常可在1-3小时内完成,产率良好。

相似文献

1
Palladium(0)-catalyzed, copper(i)-mediated coupling of cyclic thioamides with alkenylboronic acids, organostannanes, and siloxanes.钯(0)催化、铜(I)介导的环状硫代酰胺与烯基硼酸、有机锡烷和硅氧烷的偶联反应。
J Org Chem. 2009 Jul 17;74(14):5118-21. doi: 10.1021/jo900848s.
2
Palladium(0)-catalyzed, copper(I)-mediated coupling of boronic acids with cyclic thioamides. selective carbon-carbon bond formation for the functionalization of heterocycles.钯(0)催化、铜(I)介导的硼酸与环状硫代酰胺的偶联反应。用于杂环官能化的选择性碳-碳键形成。
J Org Chem. 2007 Jun 8;72(12):4440-8. doi: 10.1021/jo070408f. Epub 2007 May 11.
3
The Liebeskind-Srogl C-C cross-coupling reaction.利伯斯金德-施罗格尔碳-碳交叉偶联反应
Angew Chem Int Ed Engl. 2009;48(13):2276-86. doi: 10.1002/anie.200802842.
4
Palladium-catalyzed copper(I)-mediated cross-coupling of arylboronic acids and 2(1H)-pyrazinones facilitated by microwave irradiation with simultaneous cooling.钯催化、铜(I)介导的芳基硼酸与2(1H)-吡嗪酮的交叉偶联反应,通过微波辐射并同时冷却来促进。
Org Biomol Chem. 2007 Sep 21;5(18):2962-5. doi: 10.1039/b704389a. Epub 2007 Aug 6.
5
Copper/amino acid catalyzed cross-couplings of aryl and vinyl halides with nucleophiles.铜/氨基酸催化的芳基卤化物和乙烯基卤化物与亲核试剂的交叉偶联反应。
Acc Chem Res. 2008 Nov 18;41(11):1450-60. doi: 10.1021/ar8000298.
6
Ketone synthesis under neutral conditions. Cu(I) diphenylphosphinate-mediated, palladium-catalyzed coupling of thiol esters and organostannanes.中性条件下的酮合成。二苯基次膦酸亚铜介导、钯催化的硫醇酯与有机锡烷的偶联反应。
Org Lett. 2003 Aug 21;5(17):3033-5. doi: 10.1021/ol034962x.
7
Palladium-catalyzed desulfitative Mizoroki-Heck couplings of sulfonyl chlorides with mono- and disubstituted olefins: rhodium-catalyzed desulfitative heck-type reactions under phosphine- and base-free conditions.钯催化磺酰氯与单取代和双取代烯烃的脱硫化 Mizoroki-Heck 偶联反应:在无膦和无碱条件下的铑催化脱硫化 Heck 型反应。
Chemistry. 2005 Apr 22;11(9):2633-41. doi: 10.1002/chem.200400838.
8
Selective cross-couplings. Sequential Stille-Liebeskind/Srogl reactions of 3-chloro-4-arylthiocyclobutene-1,2-dione.选择性交叉偶联。3-氯-4-芳硫基环丁烯-1,2-二酮的连续施蒂勒-利贝斯金德/斯罗格反应。
Org Lett. 2007 Oct 11;9(21):4163-6. doi: 10.1021/ol701628z. Epub 2007 Sep 14.
9
Palladium pincer complex catalyzed cross-coupling of vinyl epoxides and aziridines with organoboronic acids.钯钳形配合物催化环氧乙烯和氮杂环丙烷与有机硼酸的交叉偶联反应。
Chemistry. 2005 Sep 5;11(18):5260-8. doi: 10.1002/chem.200500270.
10
Tunable carbon-carbon and carbon-sulfur cross-coupling of boronic acids with 3,4-dihydropyrimidine-2-thiones.硼酸与3,4-二氢嘧啶-2-硫酮的可调碳-碳和碳-硫交叉偶联
Org Lett. 2004 Mar 4;6(5):771-4. doi: 10.1021/ol036496h.

引用本文的文献

1
Copper-promoted dehydrosulfurative carbon-nitrogen cross-coupling with concomitant aromatization for synthesis of 2-aminopyrimidines.铜促进的脱氢脱硫碳-氮交叉偶联反应及伴随的芳构化反应用于合成2-氨基嘧啶。
RSC Adv. 2022 Dec 20;13(1):172-177. doi: 10.1039/d2ra05180j. eCollection 2022 Dec 19.
2
1H-Imidazol-4(5H)-ones and thiazol-4(5H)-ones as emerging pronucleophiles in asymmetric catalysis.1H-咪唑-4(5H)-酮和噻唑-4(5H)-酮作为不对称催化中新兴的亲核前体。
Beilstein J Org Chem. 2016 May 9;12:918-36. doi: 10.3762/bjoc.12.90. eCollection 2016.
3
Parallel microwave chemistry in silicon carbide microtiter platforms: a review.
碳化硅微滴板中的平行微波化学:综述。
Mol Divers. 2012 Feb;16(1):5-25. doi: 10.1007/s11030-011-9346-x. Epub 2011 Nov 30.