• 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

钯催化通过一锅法N-芳基化和氧化联芳基偶联直接合成咔唑：合成与机理研究

Palladium-catalyzed direct synthesis of carbazoles via one-pot N-arylation and oxidative biaryl coupling: synthesis and mechanistic study.

作者信息

Watanabe Toshiaki, Oishi Shinya, Fujii Nobutaka, Ohno Hiroaki

机构信息

Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.

出版信息

J Org Chem. 2009 Jul 3;74(13):4720-6. doi: 10.1021/jo9003376.

DOI:10.1021/jo9003376
PMID:19489575
Abstract

An efficient catalytic system has been developed for the synthesis of carbazoles by one-pot N-arylation and oxidative biaryl coupling. A significant substituent effect of the diarylamine intermediate on oxidative coupling was observed. Mechanistic studies of oxidative coupling, including trapping of reaction intermediates and kinetic isotope effect experiments, are also presented.

摘要

已经开发出一种高效的催化体系，用于通过一锅法N-芳基化和氧化联芳基偶联来合成咔唑。观察到二芳基胺中间体对氧化偶联有显著的取代基效应。还介绍了氧化偶联的机理研究，包括反应中间体的捕获和动力学同位素效应实验。

相似文献

1
Palladium-catalyzed direct synthesis of carbazoles via one-pot N-arylation and oxidative biaryl coupling: synthesis and mechanistic study.钯催化通过一锅法N-芳基化和氧化联芳基偶联直接合成咔唑：合成与机理研究
J Org Chem. 2009 Jul 3;74(13):4720-6. doi: 10.1021/jo9003376.
2
One-pot synthesis of carbazoles by palladium-catalyzed N-arylation and oxidative coupling.钯催化的N-芳基化和氧化偶联一锅法合成咔唑
Chem Commun (Camb). 2007 Nov 21(43):4516-8. doi: 10.1039/b707899d. Epub 2007 Sep 5.
3
Pd-catalyzed intramolecular oxidative C-H amination: synthesis of carbazoles.钯催化的分子内氧化 C-H 胺化反应：咔唑的合成。
Org Lett. 2011 Jul 15;13(14):3738-41. doi: 10.1021/ol201416u. Epub 2011 Jun 14.
4
Intramolecular Pd(II)-catalyzed oxidative biaryl synthesis under air: reaction development and scope.空气中分子内钯（II）催化的氧化联芳基合成：反应开发与范围
J Org Chem. 2008 Jul 4;73(13):5022-8. doi: 10.1021/jo800596m. Epub 2008 Jun 11.
5
Oxidative Pd(II)-catalyzed C-H bond amination to carbazole at ambient temperature.室温下氧化钯（II）催化的C-H键胺化反应合成咔唑
J Am Chem Soc. 2008 Dec 3;130(48):16184-6. doi: 10.1021/ja806543s.
6
Fused ring construction around pyrrole, indole, and related compounds via palladium-catalyzed oxidative coupling with alkynes.通过钯催化的与炔烃的氧化偶联反应构建围绕吡咯、吲哚及相关化合物的稠环结构。
J Org Chem. 2009 Oct 2;74(19):7481-8. doi: 10.1021/jo9016698.
7
Palladium-catalyzed regioselective oxidative coupling of indoles and one-pot synthesis of acetoxylated biindolyls.钯催化吲哚的区域选择性氧化偶联及一锅法合成乙酰氧基双吲哚。
J Org Chem. 2010 Jan 1;75(1):170-7. doi: 10.1021/jo902265s.
8
Palladium(II)-catalyzed one-pot syntheses of 9-(pyridin-2-yl)-9H-carbazoles through a tandem C-H activation/C-X (X=C or N) formation process.钯（II）催化一锅法通过串联 C-H 活化/C-X（X=C 或 N）形成过程合成 9-(吡啶-2-基)-9H-咔唑。
Chemistry. 2011 Nov 25;17(48):13613-20. doi: 10.1002/chem.201101528. Epub 2011 Oct 24.
9
Synthesis of 3-aryl-8-oxo-5,6,7,8-tetrahydroindolizines via a palladium-catalyzed arylation and heteroarylation.通过钯催化的芳基化和杂芳基化反应合成3-芳基-8-氧代-5,6,7,8-四氢中氮茚
J Org Chem. 2009 Apr 17;74(8):3160-3. doi: 10.1021/jo802768n.
10
A trifunctional catalyst for one-pot synthesis of chiral diols via Heck coupling-N-oxidation-asymmetric dihydroxylation: application for the synthesis of diltiazem and taxol side chain.一种用于通过Heck偶联-N-氧化-不对称二羟基化一锅法合成手性二醇的三功能催化剂：在合成地尔硫卓和紫杉醇侧链中的应用。
J Org Chem. 2003 Mar 7;68(5):1736-46. doi: 10.1021/jo026687i.

引用本文的文献

1
A Chemo- and Regioselective Tandem [3 + 2]Heteroannulation Strategy for Carbazole Synthesis: Combining Two Mechanistically Distinct Bond-Forming Processes.一种用于咔唑合成的化学和区域选择性串联[3+2]杂环化策略：结合两种机制上不同的成键过程。
J Org Chem. 2022 Apr 1;87(7):4603-4616. doi: 10.1021/acs.joc.1c02943. Epub 2022 Mar 18.
2
Expanding the Diversity at the C-4 Position of Pyrido[2,3-]pyrimidin-7(8)-ones to Achieve Biological Activity against ZAP-70.扩展吡啶并[2,3 - ]嘧啶 - 7(8) - 酮C - 4位的多样性以实现对ZAP - 70的生物活性。
Pharmaceuticals (Basel). 2021 Dec 15;14(12):1311. doi: 10.3390/ph14121311.
3
Visible Light Induced Metal-Free Carbene -Carbazolation.
可见光诱导的无金属卡宾-咔唑化反应
J Org Chem. 2019 Sep 6;84(17):11316-11322. doi: 10.1021/acs.joc.9b01753. Epub 2019 Aug 15.
4
Direct synthesis of aryl-annulated []carbazoles by gold(i)-catalysed cascade reaction of azide-diynes and arenes.通过金（I）催化的叠氮二炔与芳烃的串联反应直接合成芳基稠合的[]咔唑。
Chem Sci. 2018 Sep 10;9(44):8416-8425. doi: 10.1039/c8sc03525c. eCollection 2018 Nov 28.
5
Heterocycle Formation Palladium-Catalyzed C-H Functionalization.杂环形成 钯催化的C-H官能化
Synthesis (Stuttg). 2012 Jun;44(12):1778-1791. doi: 10.1055/s-0031-1289766. Epub 2012 May 25.
6
DESIGN, SYNTHESIS, AND EVALUATION OF CARBAZOLE ANALOGS AS POTENTIAL CYTOCHROME P450 INHIBITORS.咔唑类似物作为潜在细胞色素P450抑制剂的设计、合成及评估
J Undergrad Chem Res. 2013 Sep;12(4):92-95.
7
Palladium-catalyzed synthesis of natural and unnatural 2-, 5-, and 7-oxygenated carbazole alkaloids from N-arylcyclohexane enaminones.钯催化的 N-芳基环己烯亚胺酮合成天然和非天然的 2-、5-和 7-氧代咔唑生物碱。
Molecules. 2013 Aug 26;18(9):10334-51. doi: 10.3390/molecules180910334.
8
Development of a two-step route to 3-PBC and βCCt, two agents active against alcohol self-administration in rodent and primate models.开发两步法制备 3-PBC 和 βCCt，这两种药物在啮齿动物和灵长类动物模型中均能有效对抗酒精自我给药。
J Org Chem. 2011 Jun 3;76(11):4721-7. doi: 10.1021/jo200425m. Epub 2011 May 4.
9
A potent chemotherapeutic strategy in prostate cancer: S-(methoxytrityl)-L-cysteine, a novel Eg5 inhibitor.一种有效的前列腺癌化疗策略：S-（甲氧基三苯甲基）-L-半胱氨酸，一种新型的 Eg5 抑制剂。
Asian J Androl. 2011 Mar;13(2):236-41. doi: 10.1038/aja.2010.171. Epub 2011 Feb 7.