• 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

水相中通过金催化的C-H活化实现醛、炔烃和胺的高效三组分偶联反应。

A highly efficient three-component coupling of aldehyde, alkyne, and amines via C-H activation catalyzed by gold in water.

作者信息

Wei Chunmei, Li Chao-Jun

机构信息

Department of Chemistry, Tulane University, New Orleans, Louisiana 70118, USA.

出版信息

J Am Chem Soc. 2003 Aug 13;125(32):9584-5. doi: 10.1021/ja0359299.

DOI:10.1021/ja0359299
PMID:12904013
Abstract

A highly efficient three-component-coupling of aldehyde, alkyne, and amine (A3 Coupling) catalyzed by gold via C-H activation was developed in water. The reaction is general, and nearly quantitative yields of the corresponding propargylamines were obtained in most cases. Both aromatic and aliphatic aldehydes and amines can be used for the reaction. No additional cocatalyst or activator is required. A mechanistic rationale for the reaction has been proposed.

摘要

在水中开发了一种由金通过C-H活化催化的醛、炔烃和胺的高效三组分偶联反应(A3偶联反应)。该反应具有通用性,在大多数情况下,相应的炔丙胺几乎能定量生成。芳香醛和脂肪醛以及胺均可用于该反应。无需额外的助催化剂或活化剂。已提出该反应的机理依据。

相似文献

1
A highly efficient three-component coupling of aldehyde, alkyne, and amines via C-H activation catalyzed by gold in water.水相中通过金催化的C-H活化实现醛、炔烃和胺的高效三组分偶联反应。
J Am Chem Soc. 2003 Aug 13;125(32):9584-5. doi: 10.1021/ja0359299.
2
Microwave-promoted three-component coupling of aldehyde, alkyne, and amine via C-H activation catalyzed by copper in water.微波促进水中铜催化的醛、炔和胺通过C-H活化的三组分偶联反应。
Org Lett. 2004 Mar 18;6(6):1001-3. doi: 10.1021/ol049936t.
3
The first silver-catalyzed three-component coupling of aldehyde, alkyne, and amine.首例银催化的醛、炔和胺的三组分偶联反应。
Org Lett. 2003 Nov 13;5(23):4473-5. doi: 10.1021/ol035781y.
4
Indium-catalyzed highly efficient three-component coupling of aldehyde, alkyne, and amine via C-H bond activation.铟催化的通过C-H键活化实现醛、炔烃和胺的高效三组分偶联反应。
J Org Chem. 2009 Jun 5;74(11):4364-7. doi: 10.1021/jo900507v.
5
Phosphine-triggered complete chemo-switch: from efficient aldehyde-alkyne-amine coupling to efficient aldehyde-alkyne coupling in water.磷化氢引发的完全化学转换:在水中从高效的醛-炔-胺偶联到高效的醛-炔偶联。
Org Lett. 2005 Sep 29;7(20):4395-8. doi: 10.1021/ol051575+.
6
Gold(III) Salen complex-catalyzed synthesis of propargylamines via a three-component coupling reaction.金(III)双水杨醛缩乙二胺配合物催化通过三组分偶联反应合成炔丙胺。
Org Lett. 2006 Apr 13;8(8):1529-32. doi: 10.1021/ol0528641.
7
Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine.通过铜催化磺酰叠氮化物、炔烃和胺的三组分偶联高效一锅法合成N-磺酰脒。
J Am Chem Soc. 2005 Feb 23;127(7):2038-9. doi: 10.1021/ja0432968.
8
Copper-catalyzed coupling of tertiary aliphatic amines with terminal alkynes to propargylamines via C-H activation.通过C-H活化实现铜催化叔脂肪胺与末端炔烃偶联生成炔丙胺。
J Org Chem. 2008 May 16;73(10):3961-3. doi: 10.1021/jo800279j. Epub 2008 Apr 12.
9
An efficient synthesis of propargylamines via C-H activation catalyzed by copper(I) in ionic liquids.离子液体中铜(I)催化的C-H活化高效合成炔丙胺
Chem Commun (Camb). 2005 Mar 14(10):1315-7. doi: 10.1039/b416268d. Epub 2005 Jan 20.
10
Gold-nanoparticle-catalyzed synthesis of propargylamines: the traditional A3-multicomponent reaction performed as a two-step flow process.金纳米粒子催化的炔丙胺合成:作为两步流动过程进行的传统 A3 多组分反应。
Chemistry. 2011 Mar 1;17(10):3005-10. doi: 10.1002/chem.201002043. Epub 2011 Jan 31.

引用本文的文献

1
Oxidative Dehydrogenation of N-Heteroaromatic Alkyl Alcohols and Amines Facilitated by Dearomative Tautomerization.通过去芳香化互变异构促进的N-杂芳基烷基醇和胺的氧化脱氢反应
Chemistry. 2025 Jul 11;31(39):e202501531. doi: 10.1002/chem.202501531. Epub 2025 Jun 4.
2
Divergent alkynylative difunctionalization of amide bonds through C-O deoxygenation versus C-N deamination.通过C-O脱氧与C-N脱氨实现酰胺键的发散性炔基化双官能团化反应。
Nat Commun. 2025 Feb 3;16(1):1294. doi: 10.1038/s41467-024-55618-8.
3
High-throughput synthesis and optimization of ionizable lipids through A coupling for efficient mRNA delivery.
通过 A 耦联实现可电离脂质的高通量合成和优化,以提高 mRNA 的递送效率。
J Nanobiotechnology. 2024 Nov 4;22(1):672. doi: 10.1186/s12951-024-02919-1.
4
Spontaneous Water-Promoted Self-Aggregation of a Hydrophilic Gold(I) Complex Due to Ligand Sphere Rearrangement.由于配体球重排,亲水性金(I)配合物的自发水促进自聚集。
Molecules. 2023 Jul 27;28(15):5680. doi: 10.3390/molecules28155680.
5
Synthesis of Ag-Cu-Ni Nanoparticles Stabilized on Functionalized g-CN and Investigation of Its Catalytic Activity in the A-Coupling Reaction.负载于功能化g-CN上的Ag-Cu-Ni纳米粒子的合成及其在A-偶联反应中的催化活性研究
ACS Omega. 2023 May 15;8(21):18685-18694. doi: 10.1021/acsomega.3c00572. eCollection 2023 May 30.
6
Gold nanoparticle decorated post-synthesis modified UiO-66-NH for A-coupling preparation of propargyl amines.金纳米颗粒修饰后合成改性 UiO-66-NH 用于 A-偶联制备炔丙胺。
Sci Rep. 2023 Jun 3;13(1):9051. doi: 10.1038/s41598-023-35848-4.
7
Efficient access to general α-tertiary amines via water-accelerated organocatalytic multicomponent allylation.通过水加速的有机催化多组分烯丙基化反应高效获得一般的α-叔胺。
Nat Commun. 2022 May 16;13(1):2702. doi: 10.1038/s41467-022-30281-z.
8
Green synthesis of Au nanoparticles using an aqueous extract of and their catalytic performance for alkyne/aldehyde/amine A coupling reactions.使用[具体物质]水提取物绿色合成金纳米颗粒及其对炔烃/醛/胺A偶联反应的催化性能。 (注:原文中“using an aqueous extract of ”这里有缺失内容)
RSC Adv. 2018 Nov 14;8(67):38186-38195. doi: 10.1039/c8ra06819d.
9
Recyclable Cu/CN composite catalyzed AHA/A coupling reactions for the synthesis of propargylamines.可回收的铜/碳氮复合材料催化α-羟基酸/炔丙醇偶联反应合成炔丙胺。
RSC Adv. 2018 Sep 24;8(57):32942-32947. doi: 10.1039/c8ra06613b. eCollection 2018 Sep 18.
10
A comparative study on atomically precise Au nanoclusters as catalysts for the aldehyde-alkyne-amine (A) coupling reaction: ligand effects on the nature of the catalysis and efficiency.原子精确的金纳米团簇作为醛-炔-胺(A)偶联反应催化剂的比较研究:配体对催化性质和效率的影响。
RSC Adv. 2019 Feb 13;9(10):5475-5479. doi: 10.1039/c9ra00933g. eCollection 2019 Feb 11.