• 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

钌催化的各种芳基羧酸与芳基和杂芳基卤化物的 C-H 芳基化反应。

Ruthenium-Catalyzed C-H Arylation of Diverse Aryl Carboxylic Acids with Aryl and Heteroaryl Halides.

机构信息

University of Rochester , Rochester, New York 14627-0216, United States.

出版信息

Org Lett. 2016 Oct 21;18(20):5432-5435. doi: 10.1021/acs.orglett.6b02862. Epub 2016 Oct 13.

DOI:10.1021/acs.orglett.6b02862
PMID:27736085
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5079292/
Abstract

Ruthenium ligated to tricyclohexylphosphine or di-tert-butylbipyridine catalyzes the arylation of carboxylic acids with diverse aryl halides (iodide, bromide, and triflate; aryl and heteroaryl). In addition, arylations with 2-iodophenol formed benzochromenones, carboxylate was shown to be a stronger donor than an amide, and the arylation of a pyridine carboxylate was demonstrated. Stoichiometric studies demonstrated that the added ligand is required for reaction with the electrophile but not the C-H bond.

摘要

钌与三环己基膦或二叔丁基联吡啶配位,可催化羧酸与各种芳基卤化物(碘化物、溴化物和三氟甲磺酸酯;芳基和杂芳基)的芳基化反应。此外,用 2-碘苯酚进行的芳基化反应形成苯并色烯酮,证明羧酸盐是比酰胺更强的给体,并且还证明了吡啶羧酸酯的芳基化反应。化学计量研究表明,添加的配体是与亲电试剂反应所必需的,但不是与 C-H 键反应所必需的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f56b/5079292/7991e64dc4c5/ol-2016-02862y_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f56b/5079292/6c1870eb5142/ol-2016-02862y_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f56b/5079292/a8220b601e7d/ol-2016-02862y_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f56b/5079292/f3f96877d29f/ol-2016-02862y_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f56b/5079292/bbf604457fa8/ol-2016-02862y_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f56b/5079292/ccc49721010f/ol-2016-02862y_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f56b/5079292/7991e64dc4c5/ol-2016-02862y_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f56b/5079292/6c1870eb5142/ol-2016-02862y_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f56b/5079292/a8220b601e7d/ol-2016-02862y_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f56b/5079292/f3f96877d29f/ol-2016-02862y_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f56b/5079292/bbf604457fa8/ol-2016-02862y_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f56b/5079292/ccc49721010f/ol-2016-02862y_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f56b/5079292/7991e64dc4c5/ol-2016-02862y_0008.jpg

相似文献

1
Ruthenium-Catalyzed C-H Arylation of Diverse Aryl Carboxylic Acids with Aryl and Heteroaryl Halides.钌催化的各种芳基羧酸与芳基和杂芳基卤化物的 C-H 芳基化反应。
Org Lett. 2016 Oct 21;18(20):5432-5435. doi: 10.1021/acs.orglett.6b02862. Epub 2016 Oct 13.
2
Ruthenium(II)-catalyzed sp3 C-H bond arylation of benzylic amines using aryl halides.钌(II)催化的芳基卤代物与苄胺的 sp3 C-H 键芳基化反应。
Org Lett. 2012 Jul 20;14(14):3792-5. doi: 10.1021/ol301680v. Epub 2012 Jul 12.
3
Ruthenium-Catalyzed C-H Arylation of 1-Naphthol with Aryl and Heteroaryl Halides.钌催化 1-萘酚与芳基和杂芳基卤化物的 C-H 芳基化反应。
J Org Chem. 2019 Dec 6;84(23):15642-15647. doi: 10.1021/acs.joc.9b02075. Epub 2019 Nov 25.
4
Palladium-catalyzed α-arylation of aryl acetic acid derivatives via dienolate intermediates with aryl chlorides and bromides.钯催化芳基乙酸衍生物通过烯醇酸酯中间体与芳基氯化物和溴化物的α-芳基化反应。
Org Lett. 2015 Feb 6;17(3):410-3. doi: 10.1021/ol503545j. Epub 2015 Jan 12.
5
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.
6
Ruthenium-catalyzed transformation of aryl and alkenyl triflates to halides.钌催化芳基和烯基三氟甲磺酸酯向卤化物的转化。
J Am Chem Soc. 2012 Sep 12;134(36):14760-3. doi: 10.1021/ja307771d. Epub 2012 Aug 27.
7
Palladium-catalyzed decarboxylative coupling of quinolinone-3-carboxylic acids and related heterocyclic carboxylic acids with (hetero)aryl halides.钯催化的喹啉酮-3-羧酸和相关杂环羧酸与(杂)芳基卤化物的脱羧偶联反应。
Org Lett. 2012 Mar 16;14(6):1496-9. doi: 10.1021/ol300235k. Epub 2012 Mar 1.
8
Methods and Mechanisms for Cross-Electrophile Coupling of Csp(2) Halides with Alkyl Electrophiles.Csp(2)卤化物与烷基亲电试剂交叉亲电偶联的方法和机制
Acc Chem Res. 2015 Jun 16;48(6):1767-75. doi: 10.1021/acs.accounts.5b00057. Epub 2015 May 26.
9
2-aminopyrimidine-4,6-diol as an efficient ligand for solvent-free copper-catalyzed N-arylations of imidazoles with aryl and heteroaryl halides.2-氨基嘧啶-4,6-二醇作为一种有效的配体,用于无溶剂铜催化咪唑与芳基和杂芳基卤化物的N-芳基化反应。
J Org Chem. 2006 Oct 13;71(21):8324-7. doi: 10.1021/jo061572q.
10
A soluble base for the copper-catalyzed imidazole N-arylations with aryl halides.一种用于铜催化的咪唑与芳基卤化物进行N-芳基化反应的可溶性碱。
J Org Chem. 2005 Nov 25;70(24):10135-8. doi: 10.1021/jo051640t.

引用本文的文献

1
Ruthenium Catalyzed Ortho-Arylation Reaction of Benzoic Acids with Arylthianthrenium Salts.钌催化苯甲酸与芳基噻蒽鎓盐的邻位芳基化反应。
Angew Chem Int Ed Engl. 2025 Jun 24;64(26):e202504888. doi: 10.1002/anie.202504888. Epub 2025 May 22.
2
Copper-Promoted Intramolecular Oxidative Dehydrogenation for Synthesizing Dihydroisocoumarins and Isocoumarins.铜促进的分子内氧化脱氢反应合成二氢异香豆素和异香豆素
Molecules. 2023 Aug 29;28(17):6319. doi: 10.3390/molecules28176319.
3
Silver-Free C-H Activation: Strategic Approaches towards Realizing the Full Potential of C-H Activation in Sustainable Organic Synthesis.

本文引用的文献

1
Regioselective C-H Hydroarylation of Internal Alkynes with Arenecarboxylates: Carboxylates as Deciduous Directing Groups.区域选择性炔烃 C-H 芳基化反应:羧酸酯作为易脱落的导向基团。
Angew Chem Int Ed Engl. 2016 Jun 6;55(24):6933-7. doi: 10.1002/anie.201600894. Epub 2016 Apr 26.
2
Ru-Catalyzed C-H Arylation of Fluoroarenes with Aryl Halides.钌催化氟代芳烃与芳基卤化物的C-H芳基化反应
J Am Chem Soc. 2016 Mar 16;138(10):3596-606. doi: 10.1021/jacs.6b01615. Epub 2016 Mar 4.
3
Recent Advances in C-H Functionalization.C-H官能团化的最新进展
无银碳氢活化:实现碳氢活化在可持续有机合成中全部潜力的策略方法。
Angew Chem Int Ed Engl. 2022 Nov 25;61(48):e202210825. doi: 10.1002/anie.202210825. Epub 2022 Oct 21.
4
Oxidant-free, three-component synthesis of 7-amino-6-benzo[]chromen-6-ones under green conditions.绿色条件下7-氨基-6-苯并[]色烯-6-酮的无氧化剂三组分合成
RSC Adv. 2019 Oct 16;9(57):32946-32953. doi: 10.1039/c9ra07108c. eCollection 2019 Oct 15.
5
Palladium catalysed C-H arylation of pyrenes: access to a new class of exfoliating agents for water-based graphene dispersions.钯催化的芘的C-H芳基化反应:用于水基金刚石分散体的新型剥离剂的制备
Chem Sci. 2020 Jan 28;11(9):2472-2478. doi: 10.1039/c9sc05101e.
6
Copper-catalyzed remote C-H arylation of polycyclic aromatic hydrocarbons (PAHs).铜催化的多环芳烃(PAHs)远程C-H芳基化反应
Beilstein J Org Chem. 2020 Mar 30;16:530-536. doi: 10.3762/bjoc.16.49. eCollection 2020.
7
Ruthenium-Catalyzed C-H Arylation of 1-Naphthol with Aryl and Heteroaryl Halides.钌催化 1-萘酚与芳基和杂芳基卤化物的 C-H 芳基化反应。
J Org Chem. 2019 Dec 6;84(23):15642-15647. doi: 10.1021/acs.joc.9b02075. Epub 2019 Nov 25.
8
Highly-chemoselective step-down reduction of carboxylic acids to aromatic hydrocarbons palladium catalysis.钯催化下羧酸向芳烃的高化学选择性逐步还原反应
Chem Sci. 2019 Apr 29;10(22):5736-5742. doi: 10.1039/c9sc00892f. eCollection 2019 Jun 14.
9
-C-H arylation of fluoroarenes traceless directing group relay strategy.氟代芳烃的C-H芳基化:无痕导向基团接力策略
Chem Sci. 2018 Jul 25;9(35):7133-7137. doi: 10.1039/c8sc02417k. eCollection 2018 Sep 21.
10
Benzoate Cyclometalation Enables Oxidative Addition of Haloarenes at a Ru(II) Center.苯甲酸酯环金属化实现卤代芳烃在Ru(II)中心的氧化加成。
J Am Chem Soc. 2018 Sep 19;140(37):11836-11847. doi: 10.1021/jacs.8b08150. Epub 2018 Sep 5.
J Org Chem. 2016 Jan 15;81(2):343-50. doi: 10.1021/acs.joc.5b02818.
4
Recent Advances in the C-H-Functionalization of the Distal Positions in Pyridines and Quinolines.吡啶和喹啉远端位置的C-H官能化研究进展
Tetrahedron. 2015 Nov 18;71(46):8683-8716. doi: 10.1016/j.tet.2015.08.034. Epub 2015 Aug 19.
5
The medicinal chemist's toolbox for late stage functionalization of drug-like molecules.药物化学家用于药物样分子后期功能化的工具盒。
Chem Soc Rev. 2016 Feb 7;45(3):546-76. doi: 10.1039/c5cs00628g. Epub 2015 Oct 28.
6
Iridium-Catalyzed ortho-Arylation of Benzoic Acids with Arenediazonium Salts.铱催化的苯甲酸与芳基重氮盐的邻位芳基化反应。
Angew Chem Int Ed Engl. 2015 Oct 19;54(43):12607-11. doi: 10.1002/anie.201505769. Epub 2015 Sep 3.
7
Multimetallic catalysed cross-coupling of aryl bromides with aryl triflates.多金属催化的芳基溴化物与芳基三氟甲磺酸酯的交叉偶联反应。
Nature. 2015 Aug 27;524(7566):454-7. doi: 10.1038/nature14676. Epub 2015 Aug 17.
8
Ambient-Temperature Ortho C-H Arylation of Benzoic Acids with Aryl Iodides with Ligand-Supported Palladium Catalyst.苯甲酸与芳基碘在配体负载钯催化剂作用下的室温邻位C-H芳基化反应
Org Lett. 2015 Jul 17;17(14):3418-21. doi: 10.1021/acs.orglett.5b01398. Epub 2015 Jul 2.
9
Rhodium(III)-Catalyzed ortho C-H Heteroarylation of (Hetero)aromatic Carboxylic Acids: A Rapid and Concise Access to π-Conjugated Poly-heterocycles.铑(III)催化的(杂)芳基羧酸的邻位 C-H 杂芳基化:快速简洁地构建π-共轭多杂环化合物。
Angew Chem Int Ed Engl. 2015 Jun 8;54(24):7167-70. doi: 10.1002/anie.201501982. Epub 2015 Apr 27.
10
Rh(III)-catalyzed decarboxylative ortho-heteroarylation of aromatic carboxylic acids by using the carboxylic acid as a traceless directing group.铑(III)催化的芳香羧酸脱羧邻位杂芳基化反应,该反应使用羧酸作为无痕导向基团。
Org Lett. 2015 Apr 3;17(7):1762-5. doi: 10.1021/acs.orglett.5b00532. Epub 2015 Mar 23.