• 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

钯催化的交叉偶联反应:关于催化剂用量描述符mol%和ppm的重要性

Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm.

作者信息

Horbaczewskyj Christopher S, Fairlamb Ian J S

机构信息

University of York, Heslington, York, North Yorkshire, YO10 5DD, United Kingdom.

出版信息

Org Process Res Dev. 2022 Aug 19;26(8):2240-2269. doi: 10.1021/acs.oprd.2c00051. Epub 2022 Jul 11.

DOI:10.1021/acs.oprd.2c00051
PMID:36032362
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9396667/
Abstract

This Review examines parts per million (ppm) palladium concentrations in catalytic cross-coupling reactions and their relationship with mole percentage (mol %). Most studies in catalytic cross-coupling chemistry have historically focused on the concentration ratio between (pre)catalyst and the limiting reagent (substrate), expressed as mol %. Several recent papers have outlined the use of "ppm level" palladium as an alternative means of describing catalytic cross-coupling reaction systems. This led us to delve deeper into the literature to assess whether "ppm level" palladium is a practically useful descriptor of catalyst quantities in palladium-catalyzed cross-coupling reactions. Indeed, we conjectured that many reactions could, unknowingly, have employed low "ppm levels" of palladium (pre)catalyst, and generally, what would the spread of ppm palladium look like across a selection of studies reported across the vast array of the cross-coupling chemistry literature. In a few selected examples, we have examined other metal catalyst systems for comparison with palladium.

摘要

本综述考察了催化交叉偶联反应中百万分之一(ppm)钯的浓度及其与摩尔百分比(mol%)的关系。历史上,催化交叉偶联化学领域的大多数研究都集中在(预)催化剂与限量试剂(底物)之间的浓度比,以摩尔百分比表示。最近的几篇论文概述了使用“ppm级”钯作为描述催化交叉偶联反应体系的另一种方式。这促使我们更深入地研究文献,以评估“ppm级”钯是否是钯催化交叉偶联反应中催化剂用量的一个实际有用的描述符。事实上,我们推测许多反应可能在不知不觉中使用了低“ppm级”的钯(预)催化剂,一般来说,在大量交叉偶联化学文献报道的一系列研究中,ppm钯的分布情况会是怎样的。在一些选定的例子中,我们研究了其他金属催化剂体系以与钯进行比较。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/db7bd26466c5/op2c00051_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/be005427fb56/op2c00051_0018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/9b08feeb754c/op2c00051_0019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/24b172a4ee00/op2c00051_0020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/5998620b7eca/op2c00051_0021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/efce3cd6ab93/op2c00051_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/c8a18206a30d/op2c00051_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/251eab9a8e43/op2c00051_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/933163d5af99/op2c00051_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/0bd7eaeacc21/op2c00051_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/4190356f12f2/op2c00051_0023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/3ab9134df387/op2c00051_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/0b9e25067ae9/op2c00051_0024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/324303eb3f15/op2c00051_0025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/03421b2ce385/op2c00051_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/cc82fe2e8f79/op2c00051_0027.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/db7bd26466c5/op2c00051_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/be005427fb56/op2c00051_0018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/9b08feeb754c/op2c00051_0019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/24b172a4ee00/op2c00051_0020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/5998620b7eca/op2c00051_0021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/efce3cd6ab93/op2c00051_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/c8a18206a30d/op2c00051_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/251eab9a8e43/op2c00051_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/933163d5af99/op2c00051_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/0bd7eaeacc21/op2c00051_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/4190356f12f2/op2c00051_0023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/3ab9134df387/op2c00051_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/0b9e25067ae9/op2c00051_0024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/324303eb3f15/op2c00051_0025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/03421b2ce385/op2c00051_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/cc82fe2e8f79/op2c00051_0027.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdc3/9396667/db7bd26466c5/op2c00051_0008.jpg

相似文献

1
Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm.钯催化的交叉偶联反应:关于催化剂用量描述符mol%和ppm的重要性
Org Process Res Dev. 2022 Aug 19;26(8):2240-2269. doi: 10.1021/acs.oprd.2c00051. Epub 2022 Jul 11.
2
Well-defined N-heterocyclic carbenes-palladium(II) precatalysts for cross-coupling reactions.用于交叉偶联反应的明确的N-杂环卡宾-钯(II)预催化剂。
Acc Chem Res. 2008 Nov 18;41(11):1440-9. doi: 10.1021/ar800020y.
3
Sustainable Fe-ppm Pd nanoparticle catalysis of Suzuki-Miyaura cross-couplings in water.在水中可持续的 Fe-ppm Pd 纳米颗粒催化 Suzuki-Miyaura 交叉偶联反应。
Science. 2015 Sep 4;349(6252):1087-91. doi: 10.1126/science.aac6936.
4
"Homeopathic" palladium nanoparticle catalysis of cross carbon-carbon coupling reactions.“顺势疗法”钯纳米粒子对交叉碳-碳偶联反应的催化作用。
Acc Chem Res. 2014 Feb 18;47(2):494-503. doi: 10.1021/ar400168s. Epub 2013 Nov 11.
5
Catalyst shuttling enabled by a thermoresponsive polymeric ligand: facilitating efficient cross-couplings with continuously recyclable ppm levels of palladium.由热响应性聚合物配体实现的催化剂穿梭:促进高效交叉偶联反应并可连续循环使用ppm级钯。
Chem Sci. 2019 Jul 23;10(36):8331-8337. doi: 10.1039/c9sc02171j. eCollection 2019 Sep 28.
6
HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature.汉达磷:一种通用配体,可在室温下使钯催化的水相交叉偶联反应可持续保持百万分之一级别的低催化剂用量。
Angew Chem Int Ed Engl. 2016 Apr 11;55(16):4914-8. doi: 10.1002/anie.201510570. Epub 2016 Feb 29.
7
Palladium-Catalyzed Regioselective and Stereospecific Ring-Opening Cross-Coupling of Aziridines: Experimental and Computational Studies.钯催化氮丙啶的区域选择性和立体特异性开环交叉偶联:实验与计算研究
Acc Chem Res. 2020 Aug 18;53(8):1686-1702. doi: 10.1021/acs.accounts.0c00395. Epub 2020 Aug 6.
8
Mild and Robust Stille Reactions in Water using Parts Per Million Levels of a Triphenylphosphine-Based Palladacycle.使用百万分之几水平的三苯基膦基钯环实现温和且稳健的 Stille 反应。
Angew Chem Int Ed Engl. 2021 Feb 19;60(8):4158-4163. doi: 10.1002/anie.202014141. Epub 2021 Jan 21.
9
NPhos - an easily made, highly effective ligand designed for ppm level Pd-catalyzed Suzuki-Miyaura cross couplings in water.NPhos——一种易于制备的高效配体,专为水中百万分之一级钯催化的铃木-宫浦交叉偶联反应而设计。
Chem Sci. 2020 May 7;11(20):5205-5212. doi: 10.1039/d0sc00968g.
10
NiXantphos: a deprotonatable ligand for room-temperature palladium-catalyzed cross-couplings of aryl chlorides.NiXantphos:一种可去质子化的配体,用于室温下钯催化的芳基氯交叉偶联反应。
J Am Chem Soc. 2014 Apr 30;136(17):6276-87. doi: 10.1021/ja411855d. Epub 2014 Apr 21.

引用本文的文献

1
Is a Malleable Active Site Loop the Key to High Substrate Promiscuity? Hybrid, Biocatalytic Route to Structurally Diverse Taxoid Side Chains with Remarkable Dual Stereocontrol.可塑的活性位点环是高底物选择性的关键吗?通往具有卓越双重立体控制的结构多样紫杉烷类侧链的杂化生物催化途径。
Angew Chem Int Ed Engl. 2025 Jun 19:e202510889. doi: 10.1002/anie.202510889.
2
Ppm level palladium catalyzed regioselective remote arylation of alkenyl alcohols.百万分之一级钯催化的链烯醇区域选择性远程芳基化反应。
Chem Sci. 2025 Jun 3. doi: 10.1039/d5sc02745d.
3
Guideline for Analysis and Prevention of Contamination Catalysis.

本文引用的文献

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
General method for iron-catalyzed multicomponent radical cascades-cross-couplings.铁催化的多组分自由基级联交叉偶联的一般方法。
Science. 2021 Oct 22;374(6566):432-439. doi: 10.1126/science.abj6005. Epub 2021 Oct 21.
3
Rapid Evaluation of the Mechanism of Buchwald-Hartwig Amination and Aldol Reactions Using Intramolecular C Kinetic Isotope Effects.
污染催化分析与预防指南
Angew Chem Int Ed Engl. 2025 Jun 24;64(26):e202424425. doi: 10.1002/anie.202424425. Epub 2025 Apr 30.
4
Palladium Membrane Applications in Hydrogen Energy and Hydrogen-Related Processes.钯膜在氢能及与氢相关过程中的应用。
Polymers (Basel). 2025 Mar 12;17(6):743. doi: 10.3390/polym17060743.
5
Facile construction of distal and diversified tertiary and quaternary stereocenters.远端及多样的三级和四级立体中心的简便构建。
Proc Natl Acad Sci U S A. 2024 Dec 17;121(51):e2408541121. doi: 10.1073/pnas.2408541121. Epub 2024 Dec 12.
6
Reaction for coupling 3D molecular fragments expands the chemist's toolkit.用于偶联3D分子片段的反应扩展了化学家的工具集。
Nature. 2024 Oct;634(8034):551-553. doi: 10.1038/d41586-024-03221-8.
7
Revealing the Hidden Complexity and Reactivity of Palladacyclic Precatalysts: The P(-tolyl) Ligand Enables a Cocktail of Active Species Utilizing the Pd(II)/Pd(IV) and Pd(0)/Pd(II) Pathways for Efficient Catalysis.揭示钯环前催化剂隐藏的复杂性和反应活性:对甲苯基配体通过Pd(II)/Pd(IV)和Pd(0)/Pd(II)途径促成活性物种的混合以实现高效催化。
ACS Catal. 2024 Aug 9;14(17):12769-12782. doi: 10.1021/acscatal.4c02585. eCollection 2024 Sep 6.
8
Catalysis-Based Fluorometric Method for Semiquantifying Trace Palladium in Sulfur-Containing Compounds and Ibuprofen.基于催化作用的荧光法对半定量分析含硫化合物和布洛芬中的痕量钯
J Org Chem. 2024 Jun 7;89(11):8005-8010. doi: 10.1021/acs.joc.4c00651. Epub 2024 May 28.
9
Stabilized Palladium Nanoparticles from Bis-(-benzoylthiourea) Derived-Pd Complexes as Efficient Catalysts for Sustainable Cross-Coupling Reactions in Water.双(-苯甲酰硫脲)衍生钯配合物制备的稳定钯纳米颗粒作为水相中可持续交叉偶联反应的高效催化剂
Molecules. 2024 Mar 4;29(5):1138. doi: 10.3390/molecules29051138.
10
Evidence for Suzuki-Miyaura cross-couplings catalyzed by ligated Pd-clusters: from cradle to grave.由连接的钯簇催化的铃木-宫浦交叉偶联反应的证据:从摇篮到坟墓。
Chem Sci. 2024 Jan 15;15(8):2763-2777. doi: 10.1039/d3sc06447f. eCollection 2024 Feb 22.
利用分子内碳动力学同位素效应快速评估布赫瓦尔德-哈特维希胺化反应和羟醛缩合反应的机理
ACS Catal. 2021 Jan 1;11(1):60-67. doi: 10.1021/acscatal.0c04752. Epub 2020 Dec 11.
4
Reactivity of a Dinuclear Pd Complex [Pd(μ-PPh)(μ-OAc)(PPh)] with PPh: Implications for Cross-Coupling Catalysis Using the Ubiquitous Pd(OAc)/nPPh Catalyst System.双核钯配合物[Pd(μ-PPh)(μ-OAc)(PPh)]与三苯基膦的反应活性:对使用常见的Pd(OAc)₂/nPPh₃催化剂体系进行交叉偶联催化的启示。
Organometallics. 2021 Sep 13;40(17):2995-3002. doi: 10.1021/acs.organomet.1c00347. Epub 2021 Aug 19.
5
What can reaction databases teach us about Buchwald-Hartwig cross-couplings?反应数据库能让我们了解到关于布赫瓦尔德-哈特维希交叉偶联反应的哪些信息?
Chem Sci. 2020 Oct 20;11(48):13085-13093. doi: 10.1039/d0sc04074f. eCollection 2020 Dec 28.
6
Stability and activity of platinum nanoparticles in the oxygen electroreduction reaction: is size or uniformity of primary importance?铂纳米颗粒在氧电还原反应中的稳定性与活性:粒径还是均匀性至关重要?
Beilstein J Nanotechnol. 2021 Jun 29;12:593-606. doi: 10.3762/bjnano.12.49. eCollection 2021.
7
A Dichotomy in Cross-Coupling Site Selectivity in a Dihalogenated Heteroarene: Influence of Mononuclear Pd, Pd Clusters, and Pd Nanoparticles-the Case for Exploiting Pd Catalyst Speciation.二卤代杂芳烃交叉偶联位点选择性的二分法:单核 Pd、Pd 团簇和 Pd 纳米粒子的影响——利用 Pd 催化剂形态的实例。
J Am Chem Soc. 2021 Jun 30;143(25):9682-9693. doi: 10.1021/jacs.1c05294. Epub 2021 Jun 21.
8
Fragment-Derived Selective Inhibitors of Dual-Specificity Kinases DYRK1A and DYRK1B.片段衍生的双特异性激酶 DYRK1A 和 DYRK1B 的选择性抑制剂。
J Med Chem. 2021 Jul 8;64(13):8971-8991. doi: 10.1021/acs.jmedchem.1c00024. Epub 2021 Jun 18.
9
NPhos - an easily made, highly effective ligand designed for ppm level Pd-catalyzed Suzuki-Miyaura cross couplings in water.NPhos——一种易于制备的高效配体,专为水中百万分之一级钯催化的铃木-宫浦交叉偶联反应而设计。
Chem Sci. 2020 May 7;11(20):5205-5212. doi: 10.1039/d0sc00968g.
10
Discovery of AZD8154, a Dual PI3Kγδ Inhibitor for the Treatment of Asthma.发现 AZD8154,一种用于治疗哮喘的双重 PI3Kγδ 抑制剂。
J Med Chem. 2021 Jun 24;64(12):8053-8075. doi: 10.1021/acs.jmedchem.1c00434. Epub 2021 Jun 3.