Application of Hydrophobic Catalysts in Organic Synthesis Reactions

doi:10.6023/cjoc202406019

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (1): 136-150.DOI: 10.6023/cjoc202406019 Previous Articles Next Articles

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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)

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

Cite this article

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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Fig. & Tab. 30

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

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]

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

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

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

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

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

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]

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

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

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

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

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

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

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

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

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

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]

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

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

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]

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

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

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

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

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

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

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

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

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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