• 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

亲水性磷配体的合成及其在水相金属催化反应中的应用

Synthesis of Hydrophilic Phosphorus Ligands and Their Application in Aqueous-Phase Metal-Catalyzed Reactions.

作者信息

Schlatzer Thomas, Breinbauer Rolf

机构信息

Institute of Organic Chemistry Graz University of Technology Stremayrgasse 9 A-8010 Graz Austria phone.

出版信息

Adv Synth Catal. 2021 Feb 2;363(3):668-687. doi: 10.1002/adsc.202001278. Epub 2020 Dec 30.

DOI:10.1002/adsc.202001278
PMID:33679278
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7898532/
Abstract

Transition metal-catalyzed reactions in aqueous media are experiencing a constant increase in interest. In homogenous catalysis the use of water as a solvent offers advantages in cost, safety, the possibility of two-phase catalysis and simplified separation strategies. In the life sciences, transition metal catalysis in aqueous systems enables the ligation or modification of biopolymers in buffer systems or even in their cellular environment. In biocatalysis, aqueous systems allow the simultaneous use of enzymes and transition metal catalysts in cascade reactions. The use of water-soluble phosphine ligands still represents the most reliable and popular strategy for transferring metal catalysts into the aqueous phase. This review summarizes the recent advancements in this field since 2009 and describes current synthetic strategies for the preparation of hydrophilic phosphines and phosphites. In addition, recent applications of transition metal catalysis in aqueous solvents using these hydrophilic ligands are presented.

摘要

水相介质中的过渡金属催化反应正受到越来越多的关注。在均相催化中,使用水作为溶剂在成本、安全性、两相催化的可能性以及简化的分离策略方面具有优势。在生命科学中,水相体系中的过渡金属催化能够在缓冲体系甚至细胞环境中实现生物聚合物的连接或修饰。在生物催化中,水相体系允许在级联反应中同时使用酶和过渡金属催化剂。使用水溶性膦配体仍然是将金属催化剂转移到水相的最可靠和最常用的策略。本综述总结了自2009年以来该领域的最新进展,并描述了目前制备亲水性膦和亚磷酸酯的合成策略。此外,还介绍了使用这些亲水性配体在水相溶剂中进行过渡金属催化的最新应用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/b8326a0abb38/ADSC-363-668-g026.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/1aa9e2ee71ef/ADSC-363-668-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/43c0a0f1086a/ADSC-363-668-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/6255753caa0b/ADSC-363-668-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/165442ad185b/ADSC-363-668-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/bf22b3bb1c7b/ADSC-363-668-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/b3accb93e933/ADSC-363-668-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/35a1539ace00/ADSC-363-668-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/977639998261/ADSC-363-668-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/092491590381/ADSC-363-668-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/ac81fbd758a2/ADSC-363-668-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/a9d12cd49545/ADSC-363-668-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/b58f041cbc2a/ADSC-363-668-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/bad48bc52ea9/ADSC-363-668-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/a16242769885/ADSC-363-668-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/d2ba95c66089/ADSC-363-668-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/a3af0e70e485/ADSC-363-668-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/9c8d8532b71f/ADSC-363-668-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/5d1fb37af446/ADSC-363-668-g020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/2071068f81e2/ADSC-363-668-g021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/41b9c3413bc7/ADSC-363-668-g022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/82a40f2d8b2e/ADSC-363-668-g023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/3a98527dd977/ADSC-363-668-g024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/e7c7960b9dd3/ADSC-363-668-g025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/b8326a0abb38/ADSC-363-668-g026.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/1aa9e2ee71ef/ADSC-363-668-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/43c0a0f1086a/ADSC-363-668-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/6255753caa0b/ADSC-363-668-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/165442ad185b/ADSC-363-668-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/bf22b3bb1c7b/ADSC-363-668-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/b3accb93e933/ADSC-363-668-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/35a1539ace00/ADSC-363-668-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/977639998261/ADSC-363-668-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/092491590381/ADSC-363-668-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/ac81fbd758a2/ADSC-363-668-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/a9d12cd49545/ADSC-363-668-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/b58f041cbc2a/ADSC-363-668-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/bad48bc52ea9/ADSC-363-668-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/a16242769885/ADSC-363-668-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/d2ba95c66089/ADSC-363-668-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/a3af0e70e485/ADSC-363-668-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/9c8d8532b71f/ADSC-363-668-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/5d1fb37af446/ADSC-363-668-g020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/2071068f81e2/ADSC-363-668-g021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/41b9c3413bc7/ADSC-363-668-g022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/82a40f2d8b2e/ADSC-363-668-g023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/3a98527dd977/ADSC-363-668-g024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/e7c7960b9dd3/ADSC-363-668-g025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3e2/7898532/b8326a0abb38/ADSC-363-668-g026.jpg

相似文献

1
Synthesis of Hydrophilic Phosphorus Ligands and Their Application in Aqueous-Phase Metal-Catalyzed Reactions.亲水性磷配体的合成及其在水相金属催化反应中的应用
Adv Synth Catal. 2021 Feb 2;363(3):668-687. doi: 10.1002/adsc.202001278. Epub 2020 Dec 30.
2
Chiral diphosphine and monodentate phosphorus ligands on a spiro scaffold for transition-metal-catalyzed asymmetric reactions.用于过渡金属催化不对称反应的螺环骨架上的手性双膦和单齿磷配体
Acc Chem Res. 2008 May;41(5):581-93. doi: 10.1021/ar700137z. Epub 2008 Mar 1.
3
Ylide-Substituted Phosphines: A Platform of Strong Donor Ligands for Gold Catalysis and Palladium-Catalyzed Coupling Reactions.叶立德取代膦:金催化和钯催化偶联反应的强给体配体平台。
Acc Chem Res. 2022 Mar 1;55(5):770-782. doi: 10.1021/acs.accounts.1c00797. Epub 2022 Feb 16.
4
Arene-ruthenium(II) complexes with hydrophilic P-donor ligands: versatile catalysts in aqueous media.含有亲水性P供体配体的芳烃钌(II)配合物:水性介质中的多功能催化剂。
Dalton Trans. 2014 Sep 7;43(33):12447-62. doi: 10.1039/c4dt01494d.
5
Amino Acid-Derived Bifunctional Phosphines for Enantioselective Transformations.氨基酸衍生双功能膦配体用于对映选择性转化。
Acc Chem Res. 2016 Jul 19;49(7):1369-78. doi: 10.1021/acs.accounts.6b00163. Epub 2016 Jun 16.
6
Synthesis and Characterization of Transition Metal Complexes Supported by Phosphorus Ligands Obtained Using Hydrophosphination of Cyclic Internal Alkenes.通过环状内烯烃的氢膦化反应制备的磷配体支持的过渡金属配合物的合成与表征
Molecules. 2024 Aug 21;29(16):3946. doi: 10.3390/molecules29163946.
7
Electronic and Steric Tuning of a Prototypical Piano Stool Complex: Rh(III) Catalysis for C-H Functionalization.电子和空间效应对典型钢琴凳配合物的调谐:Rh(III)催化的 C-H 官能化反应。
Acc Chem Res. 2018 Jan 16;51(1):170-180. doi: 10.1021/acs.accounts.7b00444. Epub 2017 Dec 22.
8
Synthesis, Structure, and Applications of α-Cationic Phosphines.α-阳离子膦的合成、结构和应用。
Acc Chem Res. 2016 Sep 20;49(9):1797-805. doi: 10.1021/acs.accounts.6b00262. Epub 2016 Aug 16.
9
Continuous-Flow Catalysis Using Phosphine-Metal Complexes on Porous Polymers: Designing Ligands, Pores, and Reactors.在多孔聚合物上使用膦-金属配合物的连续流动催化:配体、孔和反应器的设计
Chempluschem. 2024 Oct;89(10):e202400039. doi: 10.1002/cplu.202400039. Epub 2024 Apr 24.
10
Synthesis of binaphthyl based phosphine and phosphite ligands.联萘基膦和膦酸酯配体的合成。
Chem Soc Rev. 2013 Aug 21;42(16):6990-7027. doi: 10.1039/c3cs60116a.

引用本文的文献

1
A new P3N ligand for Pd-catalyzed cross-couplings in water.一种用于水中钯催化交叉偶联反应的新型P3N配体。
Chem Sci. 2025 Jun 4. doi: 10.1039/d5sc02923f.
2
Electrochemical oxidative N-H/P-H cross-coupling with H evolution towards the synthesis of tertiary phosphines.电化学氧化N-H/P-H交叉偶联并析氢用于叔膦的合成
Chem Sci. 2022 Feb 14;13(10):3002-3008. doi: 10.1039/d1sc07248j. eCollection 2022 Mar 9.
3
Sterically Crowded Tris(2-(trimethylsilyl)phenyl)phosphine - Is it Still a Ligand?空间位阻较大的三(2-(三甲基硅基)苯基)膦——它还是一种配体吗?

本文引用的文献

1
Pd/BIPHEPHOS is an Efficient Catalyst for the Pd-Catalyzed -Allylation of Thiols with High -Selectivity.钯/联二萘酚膦是一种用于钯催化硫醇高选择性烯丙基化反应的高效催化剂。
Adv Synth Catal. 2020 Jan 23;362(2):331-336. doi: 10.1002/adsc.201901250. Epub 2019 Nov 7.
2
Labeling and Natural Post-Translational Modification of Peptides and Proteins via Chemoselective Pd-Catalyzed Prenylation of Cysteine.通过半胱氨酸的化学选择性 Pd 催化烯丙基化对肽和蛋白质进行标记和自然翻译后修饰。
J Am Chem Soc. 2019 Sep 18;141(37):14931-14937. doi: 10.1021/jacs.9b08279. Epub 2019 Sep 9.
3
Unusual Water-Soluble Imino Phosphine Ligand: Enamine and Imine Derivatives of 1,3,5-Triaza-7-phosphaadamantane (PTA).
Chemistry. 2022 Feb 1;28(7):e202103555. doi: 10.1002/chem.202103555. Epub 2022 Jan 5.
不寻常的水溶性亚氨基膦配体:1,3,5-三氮杂-7-磷杂金刚烷(PTA)的烯胺和亚胺衍生物。
Inorg Chem. 2018 Aug 6;57(15):9142-9152. doi: 10.1021/acs.inorgchem.8b01167. Epub 2018 Jul 26.
4
Hydrosoluble Cu(i)-DAPTA complexes: synthesis, characterization, luminescence thermochromism and catalytic activity for microwave-assisted three-component azide-alkyne cycloaddition click reaction.水溶性 Cu(i)-DAPTA 配合物的合成、表征、发光温致变色及在微波辅助的三组分叠氮-炔环加成点击反应中的催化活性。
Dalton Trans. 2018 May 29;47(21):7290-7299. doi: 10.1039/c8dt01232f.
5
A robust multifunctional ligand-controlled palladium-catalyzed carbonylation reaction in water.在水中进行稳健的多功能配体控制钯催化羰基化反应。
Chem Commun (Camb). 2018 May 15;54(40):5074-5077. doi: 10.1039/c8cc00324f.
6
Water-Soluble Palladium Reagents for Cysteine S-Arylation under Ambient Aqueous Conditions.在环境水相条件下用于半胱氨酸 S-芳基化的水溶性钯试剂。
Org Lett. 2017 Aug 18;19(16):4263-4266. doi: 10.1021/acs.orglett.7b01911. Epub 2017 Aug 4.
7
Selective Metal-Site-Guided Arylation of Proteins.蛋白质的选择性金属位点导向芳基化。
J Am Chem Soc. 2016 Jul 20;138(28):8678-81. doi: 10.1021/jacs.6b04043. Epub 2016 Jul 12.
8
Organometallic palladium reagents for cysteine bioconjugation.用于半胱氨酸生物共轭的有机金属钯试剂。
Nature. 2015 Oct 29;526(7575):687-91. doi: 10.1038/nature15739.
9
A general catalyst for Suzuki-Miyaura and Sonogashira reactions of aryl and heteroaryl chlorides in water.
Org Biomol Chem. 2014 Sep 21;12(35):6944-52. doi: 10.1039/c4ob00846d.
10
Combining the 'two worlds' of chemocatalysis and biocatalysis towards multi-step one-pot processes in aqueous media.将化学生物催化的“两个世界”结合起来,在水相介质中实现多步一锅法反应。
Curr Opin Chem Biol. 2014 Apr;19:171-9. doi: 10.1016/j.cbpa.2014.03.002. Epub 2014 Apr 5.