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由疏水催化剂介导的水相铃木偶联反应。

Aqueous Suzuki couplings mediated by a hydrophobic catalyst.

作者信息

Hong Sheng-Bo, Liang Lan-Chang

机构信息

Department of Chemistry, National Sun Yat-sen University Kaohsiung 80424 Taiwan

Department of Medicinal and Applied Chemistry, Kaohsiung Medical University Kaohsiung 80708 Taiwan.

出版信息

RSC Adv. 2022 Oct 11;12(44):28862-28866. doi: 10.1039/d2ra05230j. eCollection 2022 Oct 4.

DOI:10.1039/d2ra05230j
PMID:36320549
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9552190/
Abstract

The catalytic activity of [(PhP--CH)N]PdCl in aerobic aqueous Suzuki couplings is described. Though hydrophobic, this molecular catalyst is competent in cross-coupling reactions of arylboronic acids with a variety of electronically activated, unactivated, and deactivated aryl iodides, bromides, and chlorides upon heating in aqueous solutions under aerobic conditions to give biphenyl derivatives without the necessity of amphiphiles even in the presence of an excess amount of mercury.

摘要

描述了[(PhP--CH)N]PdCl在有氧水相铃木偶联反应中的催化活性。尽管这种分子催化剂具有疏水性,但在有氧条件下于水溶液中加热时,它能够使芳基硼酸与各种电子活化、未活化和钝化的芳基碘化物、溴化物和氯化物发生交叉偶联反应,生成联苯衍生物,即使在存在过量汞的情况下也无需两亲试剂。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9fb/9552190/c6084e0378d7/d2ra05230j-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9fb/9552190/53e7aea900ba/d2ra05230j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9fb/9552190/c6084e0378d7/d2ra05230j-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9fb/9552190/53e7aea900ba/d2ra05230j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9fb/9552190/c6084e0378d7/d2ra05230j-f2.jpg

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本文引用的文献

1
Quadrol-Pd(II) complexes: phosphine-free precatalysts for the room-temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media.四元钯(II)配合物:在水相介质中室温铃木-宫浦反应合成核苷类似物的无膦预催化剂。
Dalton Trans. 2022 Feb 8;51(6):2370-2384. doi: 10.1039/d1dt03778a.
2
Water in N-heterocyclic carbene-assisted catalysis.氮杂环卡宾辅助催化中的水。
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3
Immobilized Pd on magnetic nanoparticles bearing proline as a highly efficient and retrievable Suzuki-Miyaura catalyst in aqueous media.
固定在负载脯氨酸的磁性纳米颗粒上的钯,作为水相中高效且可回收的铃木-宫浦催化剂。
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4
Synthesis and application of water-soluble NHC transition-metal complexes.水溶性 NHC 过渡金属配合物的合成与应用。
Angew Chem Int Ed Engl. 2013 Jan 2;52(1):270-89. doi: 10.1002/anie.201205119. Epub 2012 Nov 9.
5
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.
6
Resolving heterogeneity problems and impurity artifacts in operationally homogeneous transition metal catalysts.解决操作上均相的过渡金属催化剂中的异质性问题和杂质假象。
Chem Rev. 2012 Mar 14;112(3):1536-54. doi: 10.1021/cr2002905. Epub 2011 Oct 24.
7
Magical power of transition metals: past, present, and future (Nobel Lecture).过渡金属的神奇力量:过去、现在与未来(诺贝尔演讲)
Angew Chem Int Ed Engl. 2011 Jul 18;50(30):6738-64. doi: 10.1002/anie.201101380. Epub 2011 Jun 29.
8
Cross-coupling reactions of organoboranes: an easy way to construct C-C bonds (Nobel Lecture).有机硼烷的交叉偶联反应:构建碳-碳键的简便方法(诺贝尔演讲)
Angew Chem Int Ed Engl. 2011 Jul 18;50(30):6722-37. doi: 10.1002/anie.201101379. Epub 2011 May 25.
9
Oxygen-promoted PdCl2-catalyzed ligand-free Suzuki reaction in aqueous media.水相介质中氧气促进的无配体 PdCl2 催化的 Suzuki 反应。
Org Biomol Chem. 2011 Feb 21;9(4):1054-60. doi: 10.1039/c0ob00524j. Epub 2010 Dec 13.
10
Aqueous-phase Suzuki-Miyaura cross-coupling reactions catalyzed by Pd-NHC complexes.钯-氮杂环卡宾配合物催化的水相铃木-宫浦交叉偶联反应。
Dalton Trans. 2009 Sep 21(35):7039-44. doi: 10.1039/b907032j. Epub 2009 Jul 13.