疏水型催化剂在有机合成反应中的应用

doi:10.6023/cjoc202406019

有机化学 ›› 2025, Vol. 45 ›› Issue (1): 136-150.DOI: 10.6023/cjoc202406019 上一篇下一篇

综述与进展

疏水型催化剂在有机合成反应中的应用

徐晶^a^,^b, 张娟^b, 高文超^b, 孟凡会^c, 杨朋^c^,^d, 常宏宏^b^,^e^,^*()

a 太原理工大学人工智能学院太原 030024
b 太原理工大学化学与化工学院太原 030024
c 太原理工大学省部共建煤基能源清洁高效利用国家重点实验室太原 030024
d 山东师范大学化学化工与材料科学学院济南 250014
e 山西天宏达安医药科技有限公司山西晋中 030600

收稿日期:2024-06-12 修回日期:2024-08-13 发布日期:2024-09-18
基金资助:
太原理工大学省部共建煤基能源清洁高效利用国家重点实验室开放基金(SKL202102); 山西省基础研究计划(202303021211033); 山西省基础研究计划(20210302124123)

Application of Hydrophobic Catalysts in Organic Synthesis Reactions

Jing Xu^a^,^b, Juan Zhang^b, Wenchao Gao^b, Fanhui Meng^c, Peng Yang^c^,^d, Honghong Chang^b^,^e()

a College of Artificial Intelligence, Taiyuan University of Technology, Taiyuan 030024
b College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024
c State Key Laboratory of Clean and Efficient Coal Utilization, Taiyuan University of Technology, Taiyuan 030024
d College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014
e Shanxi Tihondan Pharmaceutical Technology Co. Ltd., Jinzhong, Shanxi 030600

Received:2024-06-12 Revised:2024-08-13 Published:2024-09-18
Contact: *E-mail: changhonghong@tyut.edu.cn
Supported by:
State Key Laboratory of Clean and Efficient Coal Utilization, Taiyuan University of Technology(SKL202102); Fundamental Research Program of Shanxi Province(202303021211033); Fundamental Research Program of Shanxi Province(20210302124123)

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摘要/Abstract

在许多反应中通常不可避免地产生水或需要水, 水在反应中起着溶剂、反应物、副产物、催化剂或质子转移剂的作用, 在多相催化体系中可作为溶剂改善底物的亲水性, 进而促进反应的进行, 但在催化合成领域普遍认为水分子是一种破坏性因素, 会破坏金属活性位点, 导致催化剂性能下降甚至失活. 传统金属催化剂大多具有“水不稳定性”, 因此疏水催化剂或疏水微环境的构建及性能探究成为了研究热点. 以疏水催化剂为核心, 详细总结了以Pt、Pd、Fe、Co、Cu、Au、Ti、Rh等金属为活性位点设计并制备疏水催化剂的研究进展, 对疏水催化剂在氧化、还原、偶联及CO₂转化等有机反应中的应用进行了归纳和分析, 阐释了针对特定反应体系构建具有适宜“亲疏水效应”催化剂, 并实现目标分子高效合成面临的挑战, 并对该领域未来的发展趋势进行了展望.

关键词: 疏水改性, 催化剂, 有机合成, 应用

Water is usually inevitably produced or needed in the reaction, and it plays the roles of solvent, reactant, by-product, catalyst or proton transfer agent in the reaction. It can be used as a solvent to improve the hydrophilicity of the substrate in multiphase catalytic systems, which can promote the reaction. But in the field of catalytic synthesis, it is widely recognized that water molecule is a destructive factor, which can destroy the active sites of metals, leading to the decrease of catalyst performance or even inactivation. Most of the traditional metal catalysts are “water-unstable”, so the construction and performance of hydrophobic catalysts or hydrophobic microenvironments have become a hot research topic. In this review, the research progress of designing and preparing hydrophobic catalysts using Pt, Pd, Fe, Co, Cu, Au, Ti, Rh and other metals as active sites is summarized in detail, and the organic applications of hydrophobic catalysts in oxidation, reduction, coupling and CO₂ conversion are summarized and analyzed. It is also explained that the hydrophobic microenvironments with appropriate hydrophilic effect can be constructed for the specific reaction systems. The challenges of constructing catalysts with suitable “hydrophobic effect” for specific reaction systems and realizing efficient synthesis of target molecules are explained, and the future development trend of this field is also prospected.

Key words: hydrophobic modification, catalyst, organic synthesis, application

引用此文

徐晶, 张娟, 高文超, 孟凡会, 杨朋, 常宏宏. 疏水型催化剂在有机合成反应中的应用[J]. 有机化学, 2025, 45(1): 136-150.

Jing Xu, Juan Zhang, Wenchao Gao, Fanhui Meng, Peng Yang, Honghong Chang. Application of Hydrophobic Catalysts in Organic Synthesis Reactions[J]. Chinese Journal of Organic Chemistry, 2025, 45(1): 136-150.

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图/表 30

图1. (a)伯醇与胺的脱氢偶联及金属-配体的作用机制[10]; (b)亲疏水胶束[11]

Figure 1. (a) Dehydrogenation coupling of primary alcohols with amines and the mechanism of metal ligand interaction[10]; (b) Hydrophilic and hydrophobic micelles[11]

图式1. (a)水介质中丙烯酸甲酯催化氢化合成丙酸甲酯、(b)疏水性Pd基催化剂催化苯酚氢化合成环己酮、环己醇、(c)疏水性催化剂Pd/MCN@MS-NH2催化苯酚选择性氢化合成环己酮[37⇓-39]

Scheme 1. (a) Catalytic hydrogenation of methyl acrylate to methyl propionate in aqueous medium, (b) hydrophobic Pd based catalyst for the hydrogenation of phenol to synthesize cyclohexanone and cyclohexanol, and (c) hydrophobic catalyst Pd/MCN- @MS-NH2 catalytic selective hydrogenation of phenol to synthesize cyclohexanone[37⇓-39]

图2. 疏水性Pd/UiO-66@PDMS催化剂的制备过程[40]

Figure 2. Preparation process of hydrophobic Pd/UiO-66@- PDMS catalyst[40]

图式2. Pd/TiO2@POS催化剂催化苯乙炔加氢和苯胺还原胺化[41]

Scheme 2. Catalytic hydrogenation of phenylacetylene and reductive amination of aniline over Pd/TiO2@POS catalyst[41]

图3. 疏水性催化剂Pd1-S-C在端炔加氢反应中的应用[42]

Figure 3. Application of hydrophobic catalyst Pd1-S-C in terminal acetylene hydrogenation reaction[42]

图4. 疏水性催化剂Pd/Al2O3-PA在苯酚和蒽醌氢化反应中的应用[43]

Figure 4. Application of hydrophobic catalyst Pd/Al2O3-PA in the hydrogenation reaction of phenol and anthraquinone[43]

图5. Pt@UiO-66@GO、Pt@UiO-66@rGO催化4-硝基苯酚和硝基苯的还原[45]

Figure 5. Pt@UiO-66@GO and Pt@UiO-66@RGO catalyzed reduction reaction of 4-nitrophenol and nitrobenzene[45]

图6. (a) MIL-101、(b) MIL-101@Pt@FeP-CMPsponge和(c) MIL-101@Pt@FeP-CMP5.5的水接触角, 以及(d)肉桂醛氢化反应机理[47]

Figure 6. Water contact angles of (a) MIL-101, (b) MIL-101@Pt@FeP-CMPsponge and (c) MIL-101@Pt@FeP-CMP5.5, and (d) mechanism of cinnamaldehyde hydrogenation reaction[47]

图7. 烷基膦酸酯涂层增强γ-Al2O3催化剂载体的水热稳定性[49]

Figure 7. Enhanced hydrothermal stability of γ-Al2O3 catalyst supports with alkyl phosphonate coatings[49]

图8. 疏水性光催化剂Pt/o-PCN的催化机理(S表示空穴牺牲剂)[52]

Figure 8. Catalytic mechanism of hydrophobic photocatalyst Pt/o-PCN (S represents hole sacrificial agent)[52]

图9. 疏水催化剂Au@IB-YSN在芳香族硝基化合物还原反应中应用[53]

Figure 9. Hydrophobic catalyst Au@IB-YSN application in the reduction reaction of aromatic nitro compounds[53]

图10. 超疏水多孔亚磷酸盐配体骨架(phosphite-POP)的制备及应用性能[54]

Figure 10. Preparation and application performance of superhydrophobic porous phosphate ligand skeleton (phosphate POP)[54]

图式3. 二胺修饰Rh、Ru疏水多相催化剂在不对称催化反应中的应用[55]

Scheme 3. Application of diamine modified Rh and Ru hydrophobic multiphase catalysts in asymmetric catalytic reactions[55]

图11. 疏水性催化剂Ti-MOF@Pt@DM-LZU1的制备[56]

Figure 11. Preparation of hydrophobic catalyst Ti-MOF@Pt@- DM-LZU1[56]

图12. Au NPs负载疏水多孔碳高效电催化CO2RR反应原理[57]

Figure 12. Principles of efficient electrocatalytic CO2RR reaction by Au NPs loaded hydrophobic porous carbon[57]

图13. 疏水性Cu/ZnO催化剂在合成气转化反应中的催化机理[61]

Figure 13. Catalytic mechanism of hydrophobic catalyst Cu/ ZnO in syngas reforming reaction[61]

图14. 疏水性催化剂NiCu/SiO2-400 (C)在糠醛还原反应中的应用[64]

Figure 14. Application of hydrophobic catalyst NiCu/SiO2-400 (C) in furfural reduction reaction[64]

图式4. (a)疏水性钴基催化剂在烃类溶剂中催化醇氧化合成羧酸的反应过程、(b)催化反应机理[69]

Scheme 4. (a) Catalytic oxidation of alcohols to synthesis of carboxylic acids by hydrophobic cobalt-based catalyst in hydrocarbon solvents, and (b) propose mechanism of the catalysis[69]

图15. ZIF-8功能化Pt/C催化剂对醇的选择性电氧化反应[70]

Figure 15. Selective alcohol electrooxidation by ZIF-8 Functionalized Pt/C catalyst[70]

图16. Pt@O-ZSM-5@OTS双壳体结构示意图[71]

Figure 16. Schematic view of the for dual-shell Pt@O-ZSM- 5@OTS[71]

图17. 三个电极上的水接触角(a) Pt/C、(b) Pt/C-O-12和(c) Pt/C-F-800电极, 以及(d)微环境对N2H4电催化反应的影响[74]

Figure 17. Water contact angle on three electrodes of (a) Pt/C, (b) Pt/C-O-12 and (c) Pt/C-F-800, and (d) the influence of microenvironment on N2H4 electrocatalysis reaction[74]

图式5. 疏水Sn-Beta-F和Ti-Beta-F在醛糖-酮糖异构化反应中的应用[76]

Scheme 5. Application of hydrophobic Sn-Beta-F and Ti-Beta-F in aldose-ketose isomerization reactions[76]

图18. 疏水胶束催化剂Au@SiO2的结构示意图[77]

Figure 18. Schematic structure of the hydrophobic micellar catalyst Au@SiO2[77]

图19. 疏水性铁基催化剂的催化机理[81]

Figure 19. Catalytic mechanism of hydrophobic iron-based catalyst[81]

图20. 水介质中疏水全氟烷烃修饰金属有机骨架用于吲哚 C—H活化[82]

Figure 20. Hydrophobic perfluoroalkane-modified metal organic framework for indole C—H activation in aqueous medium[82]

图式6. 非均相疏水催化剂γ-Fe2O3-Cu-complex催化α-氨基膦酸盐合成的反应机理[83]

Scheme 6. Reaction mechanism for the synthesis of α-amino- phosphonates catalyzed by a nonhomogeneous hydrophobic catalyst γ-Fe2O3-Cu-complex[83]

图21. HPMC疏水口袋在水介质中的催化示意图[84]

Figure 21. Catalytic schematic of HPMC hydrophobic pockets in aqueous medium [84]

图22. 疏水酸性金属-有机骨架在5-羟甲基糠醛合成中的应用[85]

Figure 22. Application of hydrophobic acidic metal organic framework in the synthesis of 5-hydroxymethylfurfural[85]

图23. 疏水催化剂Rh/POPs在环己烯氢羧化反应中的应用[86]

Figure 23. Application of hydrophobic catalyst Rh/POPs in the hydrocarboxylation reaction of cyclohexene[86]

图24. 疏水功能化UiO-66催化剂在的葡萄糖转化中的应用[87]

Figure 24. Hydrophobic functionalization of UiO-66 catalyst for glucose conversion[87]

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疏水型催化剂在有机合成反应中的应用

Application of Hydrophobic Catalysts in Organic Synthesis Reactions

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