• 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

以分子氧作为唯一氧化剂的钯(II)催化氧化反应的最新进展与挑战

Recent advancements and challenges of palladium(II)-catalyzed oxidation reactions with molecular oxygen as the sole oxidant.

作者信息

Gligorich Keith M, Sigman Matthew S

机构信息

Department of Chemistry, University of Utah, Salt Lake City, UT 84112, USA.

出版信息

Chem Commun (Camb). 2009 Jul 14(26):3854-67. doi: 10.1039/b902868d. Epub 2009 May 14.

DOI:10.1039/b902868d
PMID:19662234
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2873851/
Abstract

During the past 10 years there have been significant advances in Pd(II)-catalyzed oxidation reactions where the use of ligands has led to the development of catalytic systems capable of achieving high turnover numbers, which employ molecular oxygen as the sole stoichiometric oxidant. This Feature article will highlight some of the recent developments in direct molecular oxygen-coupled Pd(II)-catalyzed oxidation reactions with an emphasis on enhanced catalytic systems and new reactions. Additionally, limitations of current catalytic systems, such as ligand oxidation, are presented and their implications for the development of new reactions are discussed.

摘要

在过去十年中,钯(II)催化的氧化反应取得了重大进展,其中配体的使用促使了能够实现高周转数的催化体系的发展,这些体系以分子氧作为唯一的化学计量氧化剂。这篇专题文章将重点介绍直接分子氧偶联钯(II)催化氧化反应的一些最新进展,着重于增强的催化体系和新反应。此外,还介绍了当前催化体系的局限性,如配体氧化,并讨论了它们对新反应开发的影响。

相似文献

1
Recent advancements and challenges of palladium(II)-catalyzed oxidation reactions with molecular oxygen as the sole oxidant.以分子氧作为唯一氧化剂的钯(II)催化氧化反应的最新进展与挑战
Chem Commun (Camb). 2009 Jul 14(26):3854-67. doi: 10.1039/b902868d. Epub 2009 May 14.
2
Palladium oxidase catalysis: selective oxidation of organic chemicals by direct dioxygen-coupled turnover.钯氧化酶催化作用:通过直接双氧偶联周转对有机化学品进行选择性氧化。
Angew Chem Int Ed Engl. 2004 Jun 28;43(26):3400-20. doi: 10.1002/anie.200300630.
3
Recent progress in Wacker oxidations: moving toward molecular oxygen as the sole oxidant.瓦克氧化反应的最新进展:向以分子氧作为唯一氧化剂迈进
Inorg Chem. 2007 Mar 19;46(6):1903-9. doi: 10.1021/ic061858d.
4
Overcoming the "oxidant problem": strategies to use O2 as the oxidant in organometallic C-H oxidation reactions catalyzed by Pd (and Cu).克服“氧化剂问题”:策略在 Pd(和 Cu)催化的有机金属 C-H 氧化反应中使用 O2 作为氧化剂。
Acc Chem Res. 2012 Jun 19;45(6):851-63. doi: 10.1021/ar2002045. Epub 2012 Jan 23.
5
Recent advances in transition-metal catalyzed reactions using molecular oxygen as the oxidant.过渡金属催化反应中利用分子氧作为氧化剂的最新进展。
Chem Soc Rev. 2012 Apr 21;41(8):3381-430. doi: 10.1039/c2cs15224j. Epub 2012 Feb 22.
6
Can Donor Ligands Make Pd(OAc) a Stronger Oxidant? Access to Elusive Palladium(II) Reduction Potentials and Effects of Ancillary Ligands via Palladium(II)/Hydroquinone Redox Equilibria.供体配体能否使 Pd(OAc)2 成为更强的氧化剂?通过 Pd(II)/对苯二酚氧化还原平衡来获得难以捉摸的钯(II)还原电势和辅助配体的影响。
J Am Chem Soc. 2020 Nov 18;142(46):19678-19688. doi: 10.1021/jacs.0c09464. Epub 2020 Nov 9.
7
Oxidation of Organic Compounds Using Water as the Oxidant with H Liberation Catalyzed by Molecular Metal Complexes.利用分子金属配合物催化水解产生的 H 作为氧化剂氧化有机化合物。
Acc Chem Res. 2022 Aug 16;55(16):2304-2315. doi: 10.1021/acs.accounts.2c00328. Epub 2022 Jul 26.
8
A palladium-catalyzed oxidative cycloaromatization of biaryls with alkynes using molecular oxygen as the oxidant.一种以分子氧为氧化剂,钯催化的联芳基与炔烃的氧化环芳构化反应。
Angew Chem Int Ed Engl. 2009;48(42):7895-8. doi: 10.1002/anie.200903975.
9
Convenient and efficient Pd-catalyzed regioselective oxyfunctionalization of terminal olefins by using molecular oxygen as sole reoxidant.使用分子氧作为唯一的再氧化剂,实现便捷高效的钯催化末端烯烃区域选择性氧官能化反应。
Angew Chem Int Ed Engl. 2006 Jan 9;45(3):481-5. doi: 10.1002/anie.200502886.
10
Mild and efficient aryl-alkenyl coupling via Pd(II) catalysis in the presence of oxygen or Cu(II) oxidants.在氧气或铜(II)氧化剂存在下通过钯(II)催化实现温和且高效的芳基-烯基偶联反应。
J Org Chem. 2002 Oct 4;67(20):7127-30. doi: 10.1021/jo020159p.

引用本文的文献

1
Mild Aerobic Oxidation of Secondary Alcohols with Water Tolerant Cu(I) Catalyst.使用耐水铜(I)催化剂对仲醇进行温和的有氧氧化
ChemSusChem. 2025 Apr 14;18(8):e202402236. doi: 10.1002/cssc.202402236. Epub 2024 Dec 13.
2
Palladium Catalysis: Dependence of the Efficiency of C-N Bond Formation on Carboxylate Ligand and Metal Carboxylate or Carboxylic Acid Additive.钯催化:C-N键形成效率对羧酸盐配体以及金属羧酸盐或羧酸添加剂的依赖性。
ACS Omega. 2024 Mar 8;9(11):12292-12306. doi: 10.1021/acsomega.4c00468. eCollection 2024 Mar 19.
3
Unified Synthesis of 2-Isocyanoallopupukeanane and 9-Isocyanopupukeanane through a "Contra-biosynthetic" Rearrangement.

本文引用的文献

1
Coupling Pd-Catalyzed Alcohol Oxidation to Olefin Functionalization: Hydrohalogenation/Hydroalkoxylation of Styrenes.钯催化的醇氧化与烯烃官能化的偶联:苯乙烯的氢卤化/氢烷氧基化反应
Organometallics. 2007 Nov 5;26(23):5680-5686. doi: 10.1021/om700675z.
2
Structural features and reactivity of (sparteine)PdCl2: a model for selectivity in the oxidative kinetic resolution of secondary alcohols.(鹰爪豆碱)二氯化钯的结构特征与反应活性:仲醇氧化动力学拆分中选择性的模型
J Am Chem Soc. 2008 Nov 26;130(47):15957-66. doi: 10.1021/ja804955e.
3
Pd-catalyzed enantioselective aerobic oxidation of secondary alcohols: applications to the total synthesis of alkaloids.
通过“反生物合成”重排实现2-异氰基别普克烷和9-异氰基普克烷的统一合成。
Angew Chem Int Ed Engl. 2024 Jan 22;63(4):e202317348. doi: 10.1002/anie.202317348. Epub 2023 Dec 20.
4
C-H bond activation concerted metalation-deprotonation at a palladium(iii) center.钯(III)中心的C-H键活化协同金属化-去质子化反应。
Chem Sci. 2023 Mar 13;14(14):3800-3808. doi: 10.1039/d3sc00034f. eCollection 2023 Apr 5.
5
Multimetallic-Catalyzed C-C Bond-Forming Reactions: From Serendipity to Strategy.多金属催化的 C-C 键形成反应:从偶然到策略。
J Am Chem Soc. 2023 Mar 29;145(12):6596-6614. doi: 10.1021/jacs.2c08615. Epub 2023 Mar 13.
6
An aerobic oxidation of alcohols into carbonyl synthons using bipyridyl-cinchona based palladium catalyst.使用基于联吡啶-金鸡纳碱的钯催化剂将醇类进行需氧氧化生成羰基合成子。
RSC Adv. 2021 Oct 6;11(52):32942-32954. doi: 10.1039/d1ra05855j. eCollection 2021 Oct 4.
7
The Three-Component Synthesis of 4-Sulfonyl-1,2,3-triazoles via a Sequential Aerobic Copper-Catalyzed Sulfonylation and Dimroth Cyclization.通过序贯有氧铜催化磺化和 Dimroth 环化反应合成 4-磺酰基-1,2,3-三唑。
Molecules. 2021 Jan 22;26(3):581. doi: 10.3390/molecules26030581.
8
Site-Selective Aerobic C-H Monoacylation of Carbazoles Using Palladium Catalysis.钯催化的咔唑的位点选择性有氧 C-H 单酰化反应。
J Org Chem. 2021 Jan 15;86(2):1396-1407. doi: 10.1021/acs.joc.0c01746. Epub 2020 Dec 31.
9
Stereoselective Remote Functionalization via Palladium-Catalyzed Redox-Relay Heck Methodologies.通过钯催化的氧化还原接力 Heck 方法实现立体选择性远程官能化。
Chemistry. 2021 Jan 4;27(1):158-174. doi: 10.1002/chem.202002849. Epub 2020 Oct 8.
10
Direct Synthesis of Chalcones from Anilides with Phenyl Vinyl Ketones by Oxidative Coupling Through C-H Bond Activation.通过C-H键活化氧化偶联由酰苯胺与苯乙烯基酮直接合成查耳酮
ACS Omega. 2018 May 18;3(5):5375-5381. doi: 10.1021/acsomega.8b00594. eCollection 2018 May 31.
钯催化仲醇的对映选择性需氧氧化:在生物碱全合成中的应用
J Am Chem Soc. 2008 Oct 15;130(41):13745-54. doi: 10.1021/ja804738b. Epub 2008 Sep 18.
4
A general and highly selective chelate-controlled intermolecular oxidative Heck reaction.一种通用且高度选择性的螯合物控制的分子间氧化Heck反应。
J Am Chem Soc. 2008 Aug 27;130(34):11270-1. doi: 10.1021/ja804120r. Epub 2008 Jul 31.
5
Palladium-catalyzed enantioselective oxidation of chiral secondary alcohols: access to both enantiomeric series.钯催化手性仲醇的对映选择性氧化:获得两种对映体系列。
Angew Chem Int Ed Engl. 2008;47(34):6367-70. doi: 10.1002/anie.200801865.
6
Basic instinct: design, synthesis and evaluation of (+)-sparteine surrogates for asymmetric synthesis.基本本能:用于不对称合成的(+)-鹰爪豆碱替代物的设计、合成与评估
Chem Commun (Camb). 2008 Feb 14(6):655-67. doi: 10.1039/b711420f.
7
Reaction of molecular oxygen with a Pd(II)-hydride to produce a Pd(II)-hydroperoxide: experimental evidence for an HX-reductive-elimination pathway.分子氧与钯(II)-氢化物反应生成钯(II)-氢过氧化物:HX还原消除途径的实验证据。
J Am Chem Soc. 2008 Apr 30;130(17):5753-62. doi: 10.1021/ja7112504. Epub 2008 Apr 5.
8
Aerobic alcohol oxidation coupled to palladium-catalyzed alkene hydroarylation with boronic esters.需氧醇氧化与钯催化的烯烃与硼酸酯的氢芳基化反应相耦合。
Angew Chem Int Ed Engl. 2008;47(17):3219-22. doi: 10.1002/anie.200705317.
9
Palladium(II)-catalyzed direct arylation of enaminones using organotrifluoroborates.钯(II)催化的烯胺酮与有机三氟硼酸盐的直接芳基化反应。
J Am Chem Soc. 2008 Mar 26;130(12):3708-9. doi: 10.1021/ja710221c. Epub 2008 Mar 6.
10
Oxygen and base-free oxidative heck reactions of arylboronic acids with olefins.芳基硼酸与烯烃的无氧无碱氧化Heck反应。
J Am Chem Soc. 2008 Feb 27;130(8):2424-5. doi: 10.1021/ja0782955. Epub 2008 Jan 31.