• 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

通过三组分偶联一锅法实现定向钴催化的C-H活化以形成C-C键和C-O键

Directed Cobalt-Catalyzed C-H Activation to Form C-C and C-O Bonds in One Pot via Three-Component Coupling.

作者信息

Li Meng-Hui, Si Xiao-Ju, Zhang He, Yang Dandan, Niu Jun-Long, Song Mao-Ping

机构信息

Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou 450001, P. R. China.

出版信息

Org Lett. 2021 Feb 5;23(3):914-919. doi: 10.1021/acs.orglett.0c04122. Epub 2021 Jan 21.

DOI:10.1021/acs.orglett.0c04122
PMID:33475370
Abstract

Herein, we disclose an efficient cobalt-catalyzed three-component coupling of benzamides, diazo compounds, and -butyl hydroperoxide, which provides an efficient approach to construct C(sp)-C(sp) and C-O bonds in one-pot accompanied with C-H activation. This protocol features low catalyst loading (4 mol %), the avoidance of additives, and excellent functional group compatibility, providing three-component coupling adducts with high yields under mild conditions (up to 88%). Mechanism studies show that the reaction may involve a radical process.

摘要

在此,我们报道了一种高效的钴催化苯甲酰胺、重氮化合物和叔丁基过氧化氢的三组分偶联反应,该反应提供了一种在一锅反应中伴随C-H活化构建C(sp)-C(sp)和C-O键的有效方法。该方法具有催化剂负载量低(4 mol%)、无需添加剂以及优异的官能团兼容性等特点,能在温和条件下以高产率(高达88%)得到三组分偶联加合物。机理研究表明该反应可能涉及自由基过程。

相似文献

1
Directed Cobalt-Catalyzed C-H Activation to Form C-C and C-O Bonds in One Pot via Three-Component Coupling.通过三组分偶联一锅法实现定向钴催化的C-H活化以形成C-C键和C-O键
Org Lett. 2021 Feb 5;23(3):914-919. doi: 10.1021/acs.orglett.0c04122. Epub 2021 Jan 21.
2
Photocatalytic Activation of Less Reactive Bonds and Their Functionalization via Hydrogen-Evolution Cross-Couplings.通过析氢交叉偶联实现低活性键的光催化活化及其功能化
Acc Chem Res. 2018 Oct 16;51(10):2512-2523. doi: 10.1021/acs.accounts.8b00267. Epub 2018 Oct 3.
3
A three component 1,3-difunctionalization of vinyl diazo esters enabled by a cobalt catalyzed C-H activation/carbene migratory insertion.钴催化的C-H活化/卡宾迁移插入实现的乙烯基重氮酯的三组分1,3-双官能化反应。
Chem Commun (Camb). 2023 May 16;59(40):6076-6079. doi: 10.1039/d3cc00295k.
4
Four-Component Radical Dual Difunctionalization (RDD) of Two Different Alkenes with Aldehydes and -Butyl Hydroperoxide (TBHP): An Easy Access to β,δ-Functionalized Ketones.四种成分的自由基双官能化(RDD)反应:通过醛和叔丁基过氧化氢(TBHP)对两种不同烯烃的双官能化反应——β,δ-官能化酮的简便获得方法。
Org Lett. 2019 Aug 2;21(15):6117-6121. doi: 10.1021/acs.orglett.9b02264. Epub 2019 Jul 19.
5
KOAc-Catalyzed One-Pot Three-Component 1,3-Dipolar Cycloaddition of α-Diazo Compounds, Nitrosoarenes, and Alkenes: An Approach to Functionalized Isoxazolidines.乙酸钾催化的α-重氮化合物、亚硝基芳烃和烯烃的一锅三组分1,3-偶极环加成反应:一种合成官能化异恶唑烷的方法。
J Org Chem. 2019 Apr 5;84(7):4402-4412. doi: 10.1021/acs.joc.9b00299. Epub 2019 Mar 19.
6
Copper-catalyzed aerobic decarboxylative coupling between cyclic α-amino acids and diverse C-H nucleophiles with low catalyst loading.铜催化的环状α-氨基酸与多种C-H亲核试剂之间的需氧脱羧偶联反应,催化剂负载量低。
RSC Adv. 2018 May 1;8(29):16202-16206. doi: 10.1039/c8ra02340a. eCollection 2018 Apr 27.
7
Catalytic diamination of olefins via N-N bond activation.通过N-N键活化实现烯烃的催化双胺化反应。
Acc Chem Res. 2014 Dec 16;47(12):3665-78. doi: 10.1021/ar500344t. Epub 2014 Nov 17.
8
Cobalt-Catalyzed Oxidative C(sp)-H Phosphonylation for α-Aminophosphonates via C(sp)-H/P(O)-H Coupling.钴催化的C(sp)-H氧化膦酰化反应通过C(sp)-H/P(O)-H偶联制备α-氨基膦酸酯
J Org Chem. 2018 Jun 15;83(12):6754-6761. doi: 10.1021/acs.joc.8b00674. Epub 2018 May 29.
9
Cobalt-Catalyzed Secondary Alkylation of Arenes and Olefins with Alkyl Ethers through the Cleavage of C(sp)-H and C(sp)-O Bonds.钴催化芳烃和烯烃与烷基醚通过C(sp)-H和C(sp)-O键的裂解进行二级烷基化反应。
J Org Chem. 2018 Nov 2;83(21):13402-13413. doi: 10.1021/acs.joc.8b02197. Epub 2018 Oct 23.
10
Transition-metal-catalyzed C-N bond forming reactions using organic azides as the nitrogen source: a journey for the mild and versatile C-H amination.过渡金属催化的以有机叠氮化物为氮源的 C-N 键形成反应:温和且多功能的 C-H 氨化反应的探索之旅。
Acc Chem Res. 2015 Apr 21;48(4):1040-52. doi: 10.1021/acs.accounts.5b00020. Epub 2015 Mar 30.

引用本文的文献

1
C-H bond activation and sequential addition to two different coupling partners: a versatile approach to molecular complexity.C-H 键活化及与两种不同偶联试剂的连续加成:一种构建分子多样性的通用方法。
Chem Soc Rev. 2022 Aug 1;51(15):6738-6756. doi: 10.1039/d2cs00012a.
2
Three-Component Coupling of Arenes, Ethylene, and Alkynes Catalyzed by a Cationic Bis(phosphine) Cobalt Complex: Intercepting Metallacyclopentenes for C-H Functionalization.三组分芳基、乙烯和炔烃的偶联反应,由阳离子双膦钴配合物催化:用于 C-H 功能化的金属环戊烯中间体的捕获。
J Am Chem Soc. 2022 Mar 16;144(10):4530-4540. doi: 10.1021/jacs.1c12646. Epub 2022 Mar 4.
3
Multicomponent Reactions Involving Diazo Reagents: A 5-Year Update.
多组分反应涉及重氮试剂:5 年更新。
Molecules. 2021 Oct 29;26(21):6563. doi: 10.3390/molecules26216563.
4
On the application of 3d metals for C-H activation toward bioactive compounds: The key step for the synthesis of silver bullets.3D金属在用于生物活性化合物的C-H活化方面的应用:合成“银弹”的关键步骤。
Beilstein J Org Chem. 2021 Jul 30;17:1849-1938. doi: 10.3762/bjoc.17.126. eCollection 2021.