• 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

通过铑催化实现(杂)芳烃与芳基碘化物的直接C-H芳基化反应。

Direct C-H arylation of (hetero)arenes with aryl iodides via rhodium catalysis.

作者信息

Yanagisawa Shuichi, Sudo Tomoko, Noyori Ryoji, Itami Kenichiro

机构信息

Department of Chemistry and Research Center for Materials Science, Nagoya University, Nagoya 464-8602, Japan.

出版信息

J Am Chem Soc. 2006 Sep 13;128(36):11748-9. doi: 10.1021/ja064500p.

DOI:10.1021/ja064500p
PMID:16953601
Abstract

A new method for the catalytic C-H arylation of heteroarenes and arenes that manifests high activity paired with reasonably broad scope was developed. Under the catalytic influence of RhCl(CO){P[OCH(CF3)2]3}2 and Ag2CO3, the direct C-H arylation of heteroarenes/arenes with aryl/heteroaryl iodides took place to afford a range of biaryls in good to excellent yields with high regioselectivity. Thiophenes, furans, pyrroles, indoles, and alkoxybenzenes are applicable in this arylation protocol.

摘要

开发了一种用于杂芳烃和芳烃催化C-H芳基化的新方法,该方法具有高活性且适用范围相当广泛。在RhCl(CO){P[OCH(CF3)2]3}2和Ag2CO3的催化作用下,杂芳烃/芳烃与芳基/杂芳基碘化物发生直接C-H芳基化反应,以良好至优异的产率和高区域选择性得到一系列联芳基化合物。噻吩、呋喃、吡咯、吲哚和烷氧基苯适用于该芳基化反应体系。

相似文献

1
Direct C-H arylation of (hetero)arenes with aryl iodides via rhodium catalysis.通过铑催化实现(杂)芳烃与芳基碘化物的直接C-H芳基化反应。
J Am Chem Soc. 2006 Sep 13;128(36):11748-9. doi: 10.1021/ja064500p.
2
Palladium-catalyzed C-H ethoxycarbonyldifluoromethylation of electron-rich heteroarenes.钯催化富电子杂芳烃的 C-H 乙氧羰基二氟甲基化反应。
Org Lett. 2015 Jun 5;17(11):2652-5. doi: 10.1021/acs.orglett.5b01024. Epub 2015 May 12.
3
Catalytic direct arylation with aryl chlorides, bromides, and iodides: intramolecular studies leading to new intermolecular reactions.与芳基氯、溴和碘的催化直接芳基化:分子内研究引发新的分子间反应
J Am Chem Soc. 2006 Jan 18;128(2):581-90. doi: 10.1021/ja055819x.
4
Oxidative C-arylation of free (NH)-heterocycles via direct (sp3) C-H bond functionalization.通过直接(sp3)C-H键官能团化实现游离(NH)-杂环的氧化C-芳基化反应。
J Am Chem Soc. 2004 Oct 20;126(41):13244-6. doi: 10.1021/ja045402b.
5
Site-specific phenylation of pyridine catalyzed by phosphido-bridged ruthenium dimer complexes: a prototype for C-H arylation of electron-deficient heteroarenes.磷桥联钌二聚体配合物催化吡啶的位点特异性苯基化:缺电子杂芳烃C-H芳基化的一个原型
J Am Chem Soc. 2005 Mar 23;127(11):3648-9. doi: 10.1021/ja042510p.
6
Aryl triflates: useful coupling partners for the direct arylation of heteroaryl derivatives via Pd-catalyzed C-H activation-functionalization.芳基三氟甲磺酸酯:通过钯催化的C-H活化官能团化实现杂芳基衍生物直接芳基化的有用偶联伙伴。
Org Biomol Chem. 2008 Jan 7;6(1):169-74. doi: 10.1039/b715235c. Epub 2007 Nov 21.
7
Synthesis of multisubstituted furans, pyrroles, and thiophenes via ynolates.通过烯醇盐合成多取代呋喃、吡咯和噻吩。
Org Lett. 2007 May 10;9(10):1963-6. doi: 10.1021/ol0705200. Epub 2007 Apr 17.
8
Rhodium-catalyzed direct oxidative carbonylation of aromatic C-H bond with CO and alcohols.铑催化芳族碳氢键与一氧化碳和醇的直接氧化羰基化反应。
J Am Chem Soc. 2009 Jan 21;131(2):729-33. doi: 10.1021/ja807167y.
9
An extremely facile synthesis of furans, pyrroles, and thiophenes by the dehydrative cyclization of propargyl alcohols.通过炔丙醇的脱水环化极其简便地合成呋喃、吡咯和噻吩。
Org Lett. 2009 Oct 15;11(20):4624-7. doi: 10.1021/ol901901m.
10
Simple copper salt-catalyzed N-arylation of nitrogen-containing heterocycles with aryl and heteroaryl halides.简单铜盐催化含氮杂环与芳基卤化物和杂芳基卤化物的N-芳基化反应。
J Org Chem. 2007 Oct 26;72(22):8535-8. doi: 10.1021/jo0712289. Epub 2007 Sep 29.

引用本文的文献

1
Direct Arylation of Simple Arenes with Aryl Bromides by Synergistic Silver and Palladium Catalysis.银钯协同催化实现简单芳烃与芳基溴的直接芳基化反应
ACS Catal. 2021 Feb 5;11(3):1430-1434. doi: 10.1021/acscatal.0c05254. Epub 2021 Jan 14.
2
Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand.铱催化的五元杂芳烃硅基化反应:吡啶基咪唑啉配体产生的高空间选择性
Angew Chem Weinheim Bergstr Ger. 2020 Apr 6;132(15):6130-6137. doi: 10.1002/ange.201916015. Epub 2020 Jan 22.
3
Oligothiophene Synthesis by a General C-H Activation Mechanism: Concerted Metalation-Deprotonation (CMD).
通过通用的C-H活化机制合成寡聚噻吩:协同金属化-去质子化(CMD)。
ACS Catal. 2019 Aug 2;9(8):6821-6836. doi: 10.1021/acscatal.9b01195. Epub 2019 Jun 24.
4
Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand.铱催化的五元杂芳烃硅基化反应:吡啶基咪唑啉配体产生的高空间选择性
Angew Chem Int Ed Engl. 2020 Apr 6;59(15):6074-6081. doi: 10.1002/anie.201916015. Epub 2020 Feb 18.
5
Synthesis of Aryl Iodides from Arylhydrazines and Iodine.由芳基肼和碘合成芳基碘化物。
ACS Omega. 2018 Aug 23;3(8):9814-9821. doi: 10.1021/acsomega.8b01559. eCollection 2018 Aug 31.
6
C-H arylation and alkenylation of imidazoles by nickel catalysis: solvent-accelerated imidazole C-H activation.镍催化咪唑的C-H芳基化和烯基化反应:溶剂加速的咪唑C-H活化反应
Chem Sci. 2015 Dec 1;6(12):6792-6798. doi: 10.1039/c5sc02942b. Epub 2015 Sep 8.
7
Synthesis and characterization of hexaarylbenzenes with five or six different substituents enabled by programmed synthesis.通过程序化合成合成并表征具有五个或六个不同取代基的六芳基苯。
Nat Chem. 2015 Mar;7(3):227-33. doi: 10.1038/nchem.2174. Epub 2015 Jan 26.
8
Palladium-catalyzed direct arylation of 5-halouracils and 5-halouracil nucleosides with arenes and heteroarenes promoted by TBAF.钯催化的 5-卤尿嘧啶和 5-卤尿嘧啶核苷与芳烃和杂芳烃的直接芳基化反应,由 TBAF 促进。
J Org Chem. 2014 May 2;79(9):4094-103. doi: 10.1021/jo500602p. Epub 2014 Apr 23.
9
Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.钯(II)催化的C-H活化/C-C交叉偶联反应:多功能性与实用性
Angew Chem Int Ed Engl. 2009;48(28):5094-115. doi: 10.1002/anie.200806273.
10
Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation.铑催化通过杂原子导向的C-H键活化形成C-C键。
Chem Rev. 2010 Feb 10;110(2):624-55. doi: 10.1021/cr900005n.