• 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

基于机理洞察的用于仲醇有氧氧化动力学拆分的钯催化剂

Palladium catalysts for aerobic oxidative kinetic resolution of secondary alcohols based on mechanistic insight.

作者信息

Jensen David R, Sigman Matthew S

机构信息

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

出版信息

Org Lett. 2003 Jan 9;5(1):63-5. doi: 10.1021/ol027190y.

DOI:10.1021/ol027190y
PMID:12509891
Abstract

The oxidative kinetic resolution of secondary alcohols has been accomplished using 1:1 complexes of PdCl(2) and N-heterocyclic carbenes. In these reactions, both achiral and chiral carbene ligands are used in conjunction with the chiral base (-)-sparteine. A general synthesis of 1:1 PdCl(2)-carbene complexes has been developed and is amenable to a wide range of carbene ligands. The potential of these complexes in aerobic oxidations is highlighted by the use of a chiral Pd(II) complex and the chiral base (-)-sparteine to enhance the kinetic resolution of a racemic alcohol. [reaction--see text]

摘要

使用PdCl₂与N-杂环卡宾的1:1配合物实现了仲醇的氧化动力学拆分。在这些反应中,非手性和手性卡宾配体均与手性碱(-)-鹰爪豆碱一起使用。已开发出一种通用的1:1 PdCl₂-卡宾配合物合成方法,该方法适用于多种卡宾配体。通过使用手性Pd(II)配合物和手性碱(-)-鹰爪豆碱来提高外消旋醇的动力学拆分效率,突出了这些配合物在需氧氧化中的潜力。[反应——见正文]

相似文献

1
Palladium catalysts for aerobic oxidative kinetic resolution of secondary alcohols based on mechanistic insight.基于机理洞察的用于仲醇有氧氧化动力学拆分的钯催化剂
Org Lett. 2003 Jan 9;5(1):63-5. doi: 10.1021/ol027190y.
2
Palladium-catalyzed aerobic oxidative kinetic resolution of alcohols with an achiral exogenous base.
J Org Chem. 2003 Sep 19;68(19):7535-7. doi: 10.1021/jo034717r.
3
Mechanistic investigations of the palladium-catalyzed aerobic oxidative kinetic resolution of secondary alcohols using (-)-sparteine.使用(-)-鹰爪豆碱对钯催化仲醇的需氧氧化动力学拆分的机理研究。
J Am Chem Soc. 2003 Jun 11;125(23):7005-13. doi: 10.1021/ja034262n.
4
Ligand-modulated palladium-catalyzed aerobic alcohol oxidations.配体调控的钯催化需氧醇氧化反应
Acc Chem Res. 2006 Mar;39(3):221-9. doi: 10.1021/ar040243m.
5
Dual role of (-)-sparteine in the palladium-catalyzed aerobic oxidative kinetic resolution of secondary alcohols.(-)-鹰爪豆碱在钯催化仲醇有氧氧化动力学拆分中的双重作用
J Am Chem Soc. 2002 Jul 17;124(28):8202-3. doi: 10.1021/ja026553m.
6
Scope of enantioselective palladium(II)-catalyzed aerobic alcohol oxidations with (-)-sparteine.使用(-)-鹰爪豆碱对映选择性钯(II)催化的需氧醇氧化反应的范围
J Org Chem. 2003 May 30;68(11):4600-3. doi: 10.1021/jo0269161.
7
Chemoenzymatic dynamic kinetic resolution of axially chiral allenes.轴手性丙二烯的化学酶动力学动态拆分。
Chemistry. 2010 Apr 19;16(15):4447-51. doi: 10.1002/chem.201000301. Epub 2010 Mar 22.
8
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.
9
Stereochemistry and mechanistic study of intramolecular Pd(II)-catalyzed oxypalladation and 1,3-chirality-transfer reactions.分子内钯(II)催化的氧钯化反应和1,3-手性转移反应的立体化学及机理研究
Chem Asian J. 2008 Feb 1;3(2):473-84. doi: 10.1002/asia.200700390.
10
Mechanistic study of alcohol oxidation by the Pd(OAc)(2)/O(2)/DMSO catalyst system and implications for the development of improved aerobic oxidation catalysts.Pd(OAc)₂/O₂/DMSO催化剂体系催化乙醇氧化的机理研究及对改进型好氧氧化催化剂开发的启示
J Am Chem Soc. 2002 Feb 6;124(5):766-7. doi: 10.1021/ja016806w.

引用本文的文献

1
The influential IPr: 25 years after its discovery.有影响力的IPr:发现25年后
Chem Sci. 2025 Jan 9;16(5):2062-2082. doi: 10.1039/d4sc07009g. eCollection 2025 Jan 29.
2
Microwave assisted synthesis of ErYbCaMoO nano-phosphor for efficient temperature sensing and catalytic applications.用于高效温度传感和催化应用的微波辅助合成铒镱钙钼酸盐纳米磷光体
Sci Rep. 2024 Nov 9;14(1):27385. doi: 10.1038/s41598-024-71478-0.
3
[Pd(NHC)(μ-Cl)Cl]: The Highly Reactive Air- and Moisture-Stable, Well-Defined Pd(II)-N-Heterocyclic Carbene (NHC) Complexes for Cross-Coupling Reactions.
[Pd(NHC)(μ-Cl)Cl]:用于交叉偶联反应的高反应活性、对空气和湿气稳定且结构明确的钯(II)-氮杂环卡宾(NHC)配合物
Acc Chem Res. 2024 Nov 19;57(22):3343-3355. doi: 10.1021/acs.accounts.4c00549. Epub 2024 Nov 6.
4
Oxidation of benzoin catalyzed by oxovanadium(IV) schiff base complexes.氧钒(IV)席夫碱配合物催化安息香的氧化反应
Chem Cent J. 2013 Jan 7;7(1):3. doi: 10.1186/1752-153X-7-3.
5
Imparting catalyst control upon classical palladium-catalyzed alkenyl C-H bond functionalization reactions.赋予经典钯催化烯基 C-H 键功能化反应催化剂控制。
Acc Chem Res. 2012 Jun 19;45(6):874-84. doi: 10.1021/ar200236v. Epub 2011 Nov 23.
6
Nickel-Catalyzed Cycloisomerization of Enynes: Catalyst Generation via C-H Activation of Carbene Ligands.镍催化烯炔的环异构化反应:通过卡宾配体的C-H活化生成催化剂
Tetrahedron. 2008 Jul 14;64(29):6870-6875. doi: 10.1016/j.tet.2008.03.071.
7
Asymmetric palladium-catalyzed hydroarylation of styrenes and dienes.不对称钯催化的苯乙烯和二烯的氢芳基化反应。
Tetrahedron. 2011 Jun 17;67(24):4435-4441. doi: 10.1016/j.tet.2011.02.027.
8
Palladium(II)-catalyzed alkene functionalization via nucleopalladation: stereochemical pathways and enantioselective catalytic applications.钯(II)催化的通过亲核钯化进行的烯烃官能团化:立体化学途径及对映选择性催化应用
Chem Rev. 2011 Apr 13;111(4):2981-3019. doi: 10.1021/cr100371y. Epub 2011 Mar 23.
9
Palladium-catalyzed hydroarylation of 1,3-dienes with boronic esters via reductive formation of pi-allyl palladium intermediates under oxidative conditions.钯催化的在氧化条件下通过还原形成π-烯丙基钯中间体的 1,3-二烯与硼酸酯的氢芳基化反应。
J Am Chem Soc. 2010 Aug 4;132(30):10209-11. doi: 10.1021/ja105010t.
10
Synthesis of Pd Complexes Bearing an Enantiomerically-Resolved Seven-Membered N-Heterocyclic Carbene Ligands and Initial Studies of their Use in Asymmetric Wacker-Type Oxidative Cyclization Reactions.具有对映体拆分的七元氮杂环卡宾配体的钯配合物的合成及其在不对称瓦克型氧化环化反应中的应用初步研究。
Tetrahedron. 2009 Jun 27;65(26):5084-5092. doi: 10.1016/j.tet.2009.04.072.