• 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

什么是交叉偶联?关于通用定义的探讨。

What is a Cross-Coupling? An Argument for a Universal Definition.

作者信息

Reimann Christopher E, Kim Kelly E, Rand Alexander W, Moghadam Farbod A, Stoltz Brian M

机构信息

California Institute of Technology, Pasadena, CA 91125.

出版信息

Tetrahedron. 2023 Jan 9;130. doi: 10.1016/j.tet.2022.133176. Epub 2022 Nov 29.

DOI:10.1016/j.tet.2022.133176
PMID:36710952
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9878734/
Abstract

Despite amazing advances in cross-coupling technologies over the past several decades, there is not a consistent definition of what a cross-coupling reaction is. Often, definitions rely on comparison to "traditional" palladium-catalyzed cross-couplings pioneered in the 1970s by chemists such as Suzuki, Negishi, and Heck. While these reactions provide a basis for a cross-coupling definition, they do not define this type of transformation, originally described by Linstead almost 20 years prior. Rather than modify and compartmentalize modern transformations to categorize them into either a synthetic or mechanistic definition, we make an argument for broadening the cross-coupling definition to to encourage discussion around exploring novel reactivity and disconnections. In addition to making a case for a universal cross-coupling definition, we cite specific examples of reactions that break the mold of prior cross-coupling definitions. We believe this perspective will stimulate dialog around what it means to be a cross-coupling and in turn inspire future developments within this field.

摘要

尽管在过去几十年里交叉偶联技术取得了惊人的进展,但对于什么是交叉偶联反应并没有一个统一的定义。通常,定义依赖于与20世纪70年代由铃木章、根岸英一和赫克等化学家开创的“传统”钯催化交叉偶联反应进行比较。虽然这些反应为交叉偶联定义提供了基础,但它们并没有定义这种类型的转化,这种转化早在近20年前就由林斯特德首次描述。我们主张拓宽交叉偶联的定义,而不是修改和划分现代转化反应,以便将它们归类为合成定义或机理定义,从而鼓励围绕探索新型反应活性和切断方式展开讨论。除了论证一个通用的交叉偶联定义外,我们还列举了一些打破先前交叉偶联定义模式的具体反应实例。我们相信这一观点将激发关于交叉偶联反应内涵的讨论,进而推动该领域未来的发展。

相似文献

1
What is a Cross-Coupling? An Argument for a Universal Definition.什么是交叉偶联?关于通用定义的探讨。
Tetrahedron. 2023 Jan 9;130. doi: 10.1016/j.tet.2022.133176. Epub 2022 Nov 29.
2
Application of Palladium-Catalyzed Cross-Coupling Reactions in Organic Synthesis.钯催化交叉偶联反应在有机合成中的应用。
Curr Org Synth. 2019;16(8):1105-1142. doi: 10.2174/1570179416666191104093533.
3
Palladium-catalyzed cross-coupling: a historical contextual perspective to the 2010 Nobel Prize.钯催化交叉偶联反应:2010 年诺贝尔化学奖的历史背景。
Angew Chem Int Ed Engl. 2012 May 21;51(21):5062-85. doi: 10.1002/anie.201107017. Epub 2012 May 9.
4
Recent advances of transition-metal catalyzed radical oxidative cross-couplings.过渡金属催化自由基氧化交叉偶联的最新进展。
Acc Chem Res. 2014 Dec 16;47(12):3459-70. doi: 10.1021/ar5002044. Epub 2014 Nov 3.
5
Palladium-Catalyzed Cross-Coupling Reactions: A Powerful Tool for the Synthesis of Agrochemicals.钯催化交叉偶联反应:合成农药的有力工具。
J Agric Food Chem. 2018 Aug 29;66(34):8914-8934. doi: 10.1021/acs.jafc.8b03792. Epub 2018 Aug 13.
6
Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki-Miyaura and Negishi Cross-Coupling Reactions for Tetra-Substituted Biaryl Synthesis.钯催化的不对称铃木-宫浦和根岸交叉偶联反应用于四取代联芳基合成的计算辅助机理研究与开发
ACS Catal. 2018 Nov 2;8(11):10190-10209. doi: 10.1021/acscatal.8b02509. Epub 2018 Sep 20.
7
The Palladium-Catalyzed Ullmann Cross-Coupling Reaction: A Modern Variant on a Time-Honored Process.钯催化的乌尔曼交叉偶联反应:一个历史悠久过程的现代变体
Acc Chem Res. 2018 Aug 21;51(8):1784-1795. doi: 10.1021/acs.accounts.8b00169. Epub 2018 Jul 16.
8
The promise and challenge of iron-catalyzed cross coupling.铁催化交叉偶联的前景与挑战
Acc Chem Res. 2008 Nov 18;41(11):1500-11. doi: 10.1021/ar800039x.
9
Decarbonylative Cross-Couplings: Nickel Catalyzed Functional Group Interconversion Strategies for the Construction of Complex Organic Molecules.脱羰交叉偶联反应:镍催化构建复杂有机分子的官能团相互转化策略
Acc Chem Res. 2018 May 15;51(5):1185-1195. doi: 10.1021/acs.accounts.8b00023. Epub 2018 Apr 13.
10
Pd-catalyzed steroid reactions.钯催化的甾体反应。
Steroids. 2015 May;97:13-44. doi: 10.1016/j.steroids.2014.07.018. Epub 2014 Aug 27.

引用本文的文献

1
The Versatile and Strategic -Carbamate Directed Metalation Group in the Synthesis of Aromatic Molecules: An Update.芳香分子合成中多功能且具策略性的——氨基甲酸酯导向金属化基团:最新进展
Chem Rev. 2024 Jun 26;124(12):7731-7828. doi: 10.1021/acs.chemrev.3c00923. Epub 2024 Jun 12.
2
Synergistic performance of a new bimetallic complex supported on magnetic nanoparticles for Sonogashira and C-N coupling reactions.负载于磁性纳米颗粒上的新型双金属配合物用于Sonogashira反应和C-N偶联反应的协同性能
Sci Rep. 2023 Oct 24;13(1):18153. doi: 10.1038/s41598-023-44168-6.

本文引用的文献

1
-Symmetric Dinickel Catalysts for Enantioselective [4 + 1]-Cycloadditions.手性双镍催化剂用于对映选择性[4+1]-环加成反应。
J Am Chem Soc. 2020 Oct 14;142(41):17294-17300. doi: 10.1021/jacs.0c08262. Epub 2020 Sep 30.
2
Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions.镍催化的对映选择性还原交叉偶联反应
ACS Catal. 2020 Aug 7;10(15):8237-8246. doi: 10.1021/acscatal.0c01842. Epub 2020 Jun 24.
3
Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis.通过镍催化实现烯基卤化物和苄基卤化物的对映选择性电还原偶联反应。
ACS Catal. 2019 Aug 2;9(8):6751-6754. doi: 10.1021/acscatal.9b01785. Epub 2019 Jul 25.
4
The Grignard Reaction - Unraveling a Chemical Puzzle.格氏反应——揭开化学谜题。
J Am Chem Soc. 2020 Feb 12;142(6):2984-2994. doi: 10.1021/jacs.9b11829. Epub 2020 Jan 30.
5
Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.交叉偶联及相关反应:将过去的成功与未来新反应的发展相联系。
Organometallics. 2019 Jan 14;38(1):3-35. doi: 10.1021/acs.organomet.8b00720. Epub 2018 Nov 27.
6
Catalytic reductive [4 + 1]-cycloadditions of vinylidenes and dienes.亚乙烯基和二烯的催化还原[4 + 1]环加成反应。
Science. 2019 Feb 22;363(6429):857-862. doi: 10.1126/science.aau0364.
7
Catalytic enantioselective aldol reactions.催化对映选择性羟醛反应。
Chem Soc Rev. 2018 Jun 18;47(12):4388-4480. doi: 10.1039/c7cs00824d.
8
Suzuki-Miyaura Coupling of Simple Ketones via Activation of Unstrained Carbon-Carbon Bonds.通过激活未受应变的碳-碳键实现简单酮的铃木-宫浦偶联反应。
J Am Chem Soc. 2018 Apr 25;140(16):5347-5351. doi: 10.1021/jacs.8b02462. Epub 2018 Apr 17.
9
Pd Metal Catalysts for Cross-Couplings and Related Reactions in the 21st Century: A Critical Review.钯金属催化剂在 21 世纪的交叉偶联反应及相关反应中的应用:批判性回顾。
Chem Rev. 2018 Feb 28;118(4):2249-2295. doi: 10.1021/acs.chemrev.7b00443. Epub 2018 Feb 20.
10
Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling.通过镍催化还原交叉偶联反应合成对映体富集的烯丙基硅烷。
J Am Chem Soc. 2018 Jan 10;140(1):139-142. doi: 10.1021/jacs.7b11707. Epub 2017 Dec 20.