重氮化合物环丙烷化用多相催化剂研究进展

doi:10.16085/j.issn.1000-6613.2022-1307

摘要/Abstract

摘要：

从重氮化合物环丙烷化用多相催化剂类型角度，将环丙烷化多相催化剂分为金属催化剂、金属负载型催化剂、络合物固载化催化剂、金属有机骨架（MOF）基催化剂等，详细介绍和评述了催化剂在活性组分、载体、固载方法、性能及作用原理等方面的研究进展。指出金属负载型催化剂制备简单，活性和选择性较高，但立体选择性差，在农药、医药领域适用性有限，更适宜应用于燃料合成领域，因此提升催化剂的稳定性和拓展金属活性组分是其发展趋势。络合物固载化催化剂具有较好的活性和立体选择性，结构与性能易于调控，但制备过程复杂，活性组分易流失，需通过优化固载方法如共价键合提高固载强度，以及优化载体孔道结构与表面基团提升载体-配体的协同作用。MOF基催化剂在环丙烷化中展现出独特的催化性能，通过机械研磨、配体掺杂、热处理等方式引入缺陷可综合提高MOF基环丙烷化催化剂性能，但需平衡活性与骨架结构的稳定性。此外，设计利于环丙烷化的手性配体并引入至MOF结构提高其立体选择性是MOF基环丙烷化催化剂的重要发展方向。

关键词: 重氮化合物, 环丙烷化, 多相催化, 固载化, 活性, 立体选择性

Abstract:

Heterogeneous cyclopropanation catalysts are classified as metal catalysts, metal-supported catalysts, complex-immobilized catalysts, and MOF-based catalysts. Research progress on the reactive components, supports, immobilization methods and action principles of heterogeneous cyclopropanation catalysts is reviewed in detail. Metal-supported catalysts are easy to prepare and have relatively high activity, selectivity but the stereoselectivity is low, therefore they show better application in fuel-synthesis than medical or pesticide. To improve the stability and expand the reactive components of metal-supported catalysts is the development tendency. Complex-immobilized catalysts have good activity and stereoselectivity with wide adjustability of structure and performance. Nevertheless, optimizing immobilization methods such as using covalent bonding and enhancing synergistic action between supports and ligands by optimizing pore structure and surface group are quite important to promote the catalyst stability and immobilizing strength. MOF-based catalysts exhibit unique properties in cyclopropanation reactions, and the catalytic performance can be improved by defect-engineering (mechanical grind, ligand doping, heat treatment, etc.) which should balance the activity and stability. Furthermore, designing chiral ligands for new MOF-based catalysts to enhance the stereoselectivity is also the important research direction.

Key words: diazo compounds, cyclopropanation, heterogeneous catalysis, immobilization, activity, stereoselectivity

中图分类号:

TQ116.2

岳鑫, 李春迎, 孙道安, 李江伟, 杜咏梅, 马辉, 吕剑. 重氮化合物环丙烷化用多相催化剂研究进展[J]. 化工进展, 2023, 42(5): 2390-2401.

YUE Xin, LI Chunying, SUN Dao’an, LI Jiangwei, DU Yongmei, MA Hui, LYU Jian. Progress on heterogeneous catalysts for cyclopropanation of diazo compounds[J]. Chemical Industry and Engineering Progress, 2023, 42(5): 2390-2401.

图/表 7

图1 卡宾中间体参与的环丙烷化反应[9-10]

图2 典型金属负载型催化剂TEM图[25-26]

图3 共聚法固载双𫫇唑啉配体[28]

图4 末端吡啶树脂轴向固载四脯氨酸二铑[58]

图5 MOF催化剂Cu2(4,4'-bpy)2SO4·6(H2O)结构及TEM图[71]

图6 利用配体掺杂在MOF结构中引入配位缺陷

图7 利用可控热缺陷工程引入配位缺陷[70]

参考文献 74

1	董慧. 环丙烷化高能量密度燃料合成研究[D]. 北京: 北京化工大学, 2021.
	DONG Hui. Synthesis of cyclopropanized high energy density fuel[D]. Beijing: Beijing University of Chemical Technology, 2021.
2	DILL James D, GREENBERG Arthur, LIEBMAN Joel F. Substituent effects on strain energies[J]. Journal of the American Chemical Society, 1979, 101(23): 6814-6826.
3	潘伦, 邓强, 鄂秀天凤, 等. 高密度航空航天燃料合成化学[J]. 化学进展, 2015, 27(11): 1531-1541.
	PAN Lun, DENG Qiang, Xiutianfeng E, et al. Synthesis chemistry of high-density fuels for aviation and aerospace propulsion[J]. Progress in Chemistry, 2015, 27(11): 1531-1541.
4	THULASIRAM H V, ERICKSON H K, POULTER C D. Chimeras of two isoprenoid synthases catalyze all four coupling reactions in isoprenoid biosynthesis[J]. Science, 2007, 316(5821): 73-76.
5	CHRISTIANSON D W. Structural and chemical biology of terpenoid cyclases[J]. Chemical Reviews, 2017, 117(17): 11570-11648.
6	ANDRES Nikolaus, WOLF Heinz, Hans ZÄHNER, et al. Stoffwechselprodukte von mikroorganismen. 253. mitteilung. hormaomycin, ein neues peptid-lacton mit morphogener aktivität auf streptomyceten[J]. Helvetica Chimica Acta, 1989, 72(3): 426-437.
7	TROTTMANN F, FRANKE J, RICHTER I, et al. Cyclopropanol warhead in malleicyprol confers virulence of human- and animal-pathogenic burkholderia species[J]. Angewandte Chemie International Edition, 2019, 58(40): 14129-14133.
8	CAPITANI Guido, HOHENESTER Erhard, FENG Liang, et al. Structure of 1-aminocyclopropane-1-carboxylate synthase, a key enzyme in the biosynthesis of the plant hormone ethylene [J]. Journal of Molecular Biology, 1999, 294(3): 745-756.
9	DENMARK Scott E, CHRISTENSON Beritte L, Diane M COE, et al. Catalytic enantioselective cyclopropanation with bis(halomethyl)zinc reagents. Ⅰ. Optimization of reaction protocol[J]. Tetrahedron Letters, 1995, 36(13): 2215-2218.
10	DEMSELBEN. Ueber die zersetzung des chloroforms durch alkoholische kalilösung[J]. Justus Liekigs Annalen Der Chemie, 1862, 123(1): 121-122.
11	BEDEKAR Ashutosh V, ANDERSSON Pher G. A new class of bis-oxazoline ligands for the Cu-catalysed asymmetric cyclopropanation of olefins[J]. Tetrahedron Letters, 1996, 37(23): 4073-4076.
12	ARLT D, JAUTELAT M, LANTZSCH R. ChemInform abstract: syntheses of pyrethroid acids[J]. Chemischer Informationsdienst, 1981, 12(51): 703-722.
13	CHEN Ying, ZHANG X Peter. Vitamin B₁₂ derivatives as natural asymmetric catalysts: enantioselective cyclopropanation of alkenes[J]. The Journal of Organic Chemistry, 2004, 69(7): 2431-2435.
14	孙越. 铁(Ⅲ)催化二氟乙醛N-磺酰腙(DFHZ)与烯烃的环丙烷化反应研究[D]. 长春: 东北师范大学, 2020.
	SUN Yue. Study on cyclopropane reaction of difluoroacetaldehyde N-sulfonylhydrazone (DFHZ) with olefins catalyzed by iron ( Ⅲ )[D]. Changchun: Northeast Normal University, 2020.
15	刘纪娜. 金属卟啉催化芳香烯烃的环丙烷化反应与机理研究[D]. 长沙: 湖南大学, 2015.
	LIU Jina. Study on cyclopropanation and mechanism of olefins catalyzed by metalloporphyrins[D]. Changsha: Hunan University, 2015.
16	边庆花, 乔振, 侯士聪, 等. 环丙烷化反应中催化剂固载化的研究进展[J]. 有机化学, 2004, 24(7): 831-841, 712.
	BIAN Qinghua, QIAO Zhen, HOU Shicong, et al. Advances of immobilization of catalysts for cyclopropanation[J]. Chinese Journal of Organic Chemistry, 2004, 24(7): 831-841, 712.
17	HANTZSCH A, SILBERRAD O. Ueber die polymerisationsproducte aus diazoessigester[J]. Berichte Der Deutschen Chemischen Gesellschaft, 1900, 33(1): 58-89.
18	HENNE Albert L, TURK Amos. Conjugated diolefins by double bond displacement[J]. Journal of the American Chemical Society, 1942, 64(4): 826-828.
19	WENKERT Ernest, GUO Ming, PIZZO Ferdinando, et al. Synthesis of 2-cycloalkenones (parts of 1,4-diacyl-1,3-butadiene systems) and of a heterocyclic analogue by metal-catalyzed decomposition of 2-diazoacylfurans[J]. Helvetica Chimica Acta, 1987, 70(5): 1429-1438.
20	CHEN Longrui, BOVEE Mark O, LEMMA Betsegaw E, et al. An inexpensive and recyclable silver-foil catalyst for the cyclopropanation of alkenes with diazoacetates under mechanochemical conditions[J]. Angewandte Chemie International Edition, 2015, 54(38): 11084-11087.
21	CHEN Longrui, LESLIE Devonna, COLEMAN Michael G, et al. Recyclable heterogeneous metal foil-catalyzed cyclopropenation of alkynes and diazoacetates under solvent-free mechanochemical reaction conditions[J]. Chemical Science, 2018, 9(20): 4650-4661.
22	FRAILE J M, GARCÍA B, GARCÍA J I, et al. The use of heterogeneous copper catalysts in cyclopropanation reactions[J]. Studies in Surface Science and Catalysis, 1997, 108: 571-578.
23	LIU Xiang, LIU Yan, LI Xiaohong, et al. Cyclopropanation on a highly active heterogeneous catalyst: CuO/TiO₂-Al₂O₃ [J]. Applied Catalysis A: General, 2003, 239(1/2): 279-286.
24	LAKSHMI KANTAM M, SWARNA JAYA V, JAYA LAKSHMI M, et al. Alumina supported copper nanoparticles for aziridination and cyclopropanation reactions[J]. Catalysis Communications, 2007, 8(12): 1963-1968.
25	ISHIKAWA Shingo, HUDSON Reuben, MASNADI Mitra, et al.Cyclopropanation of diazoesters with styrene derivatives catalyzed by magnetically recoverable copper-plated iron nanoparticles[J]. Tetrahedron, 2014, 70(36): 6162-6168.
26	SARKAR Abhijnan, FORMENTI Dario, FERRETTI Francesco, et al. Iron/N-doped graphene nano-structured catalysts for general cyclopropanation of olefins[J]. Chemical Science, 2020, 11(24): 6217-6221.
27	FELDMAN Robert A, FRAILE José M. Electrostatic immobilization of bis(oxazoline)-copper complexes on mesoporous crystalline materials: Cation exchange vs. incipient wetness methods[J]. Applied Catalysis A: General, 2014, 485: 67-73.
28	MANDOLI Alessandro, ORLANDI Simonetta, PINI Dario, et al. A reusable, insoluble polymer-bound bis(oxazoline)(IPB-box) for highly enantioselective heterogeneous cyclopropanation reactions[J]. Chemical Communications, 2003(19): 2466-2467.
29	MANDOLI Alessandro, ORLANDI Simonetta, PINI Dario, et al. Insoluble polystyrene-bound bis(oxazoline): Batch and continuous-flow heterogeneous enantioselective glyoxylate-ene reaction[J]. Tetrahedron: Asymmetry, 2004, 15(20): 3233-3244.
30	Isabel BURGUETE M, FRAILE José M, GARCÍA José I, et al. Bis(oxazoline)copper complexes covalently bonded to insoluble support as catalysts in cyclopropanation reactions[J]. The Journal of Organic Chemistry, 2001, 66(26): 8893-8901.
31	BURGUETE M I, FRAILE J M, GARCÍA-VERDUGO E, et al. Polymer-supported bis(oxazolines) and related systems: Toward new heterogeneous enantioselective catalysts[J]. Industrial & Engineering Chemistry Research, 2005, 44(23): 8580-8587.
32	WERNER Heiko, HERRERÍAS Clara I, GLOS Michael, et al. Synthesis of polymer bound azabis(oxazoline) ligands and their application in asymmetric cyclopropanations[J]. Advanced Synthesis & Catalysis, 2006, 348(1/2): 125-132.
33	MOTOYAMA Y, NISHIKATA T, NAGASHIMA H. A chiral bis(oxazoline) ligand embedded into polysiloxane gel: Application to a reusable copper catalyst for asymmetric cyclopropanation[J]. Chemistry-An Asian Journal, 2011, 6(1): 78-82.
34	FRAILE José M, GARCı́A José I, MAYORAL José A, et al. Clay-supported bis(oxazoline)-copper complexes as heterogeneous catalysts of enantioselective cyclopropanation reactions[J]. Tetrahedron: Asymmetry, 1998, 9(22): 3997-4008.
35	FERNÁNDEZ M J, FRAILE J M, GARCÍA J I, et al. Enantioselective cyclopropanation reactions promoted by immobilized bis(oxazoline)-copper complexes[J]. Topics in Catalysis, 2000, 13(3): 303-309.
36	Rosario TORVISO M, MANSILLA Daniela S, FRAILE José M, et al. The importance of copper placement in chiral catalysts supported on heteropolyanions: Lacunary vs external exchanged[J]. Molecular Catalysis, 2020, 489: 110935.
37	FRAILE José M, GARCÍA José I, MAYORAL José A, et al. Bis(oxazoline)-copper complexes, supported by electrostatic interactions, as heterogeneous catalysts for enantioselective cyclopropanation reactions: Influence of the anionic support[J]. Journal of Catalysis, 1999, 186(1): 214-221.
38	FELDMAN Robert A, FRAILE José M. Improved methodology for non-covalent immobilization of tert-butyl-azabis(oxazoline)-copper complex on Al-MCM41[J]. Applied Catalysis A: General, 2015, 502: 166-173.
39	FAKHFAKH Fatma, BARAKET Leila, GHORBEL Abdelhamid, et al. Catalytic activity of copper-bis(oxazoline) grafted on mesoporous silica in enantioselective cyclopropanation[J]. Reaction Kinetics, Mechanisms and Catalysis, 2015, 116(1): 119-130.
40	FAKHFAKH Fatma, BARAKET Leila, GHORBEL Abdelhamid, et al. Effect of support properties on the performance of silica-supported bis(oxazoline)-copper chiral complexes[J]. Journal of Molecular Catalysis A: Chemical, 2010, 329(1/2): 21-26.
41	ALBUQUERQUE Hélio, CARNEIRO Liliana, CARVALHO Ana P, et al. Enantioselective cyclopropanation and aziridination catalyzed by copper(Ⅱ) bis(oxazoline) anchored onto mesoporous materials[J]. Polyhedron, 2014, 79: 315-323.
42	SILVA Ana Rosa, ALBUQUERQUE Hélio, BORGES Susana, et al. Strategies for copper bis(oxazoline) immobilization onto porous silica based materials[J]. Microporous and Mesoporous Materials, 2012, 158: 26-38.
43	SILVA Ana Rosa, ALBUQUERQUE Hélio, FONTES André, et al. Copper bis(oxazoline) encapsulated in zeolites and its application as heterogeneous catalysts for the cyclopropanation of styrene[J]. Industrial & Engineering Chemistry Research, 2011, 50(20): 11495-11501.
44	张永忠, 钟江春, 边庆花, 等. 离子液体支载的催化剂在不对称合成反应中循环使用的研究进展[J]. 有机化学, 2006, 26(10): 1362-1369.
	ZHANG Yongzhong, ZHONG Jiangchun, BIAN Qinghua, et al. Recycle application of catalyst supported by ionic liquids to asymmetric reaction[J]. Chinese Journal of Organic Chemistry, 2006, 26(10): 1362-1369.
45	FRAILE José M, GARCÍA José I, HERRERÍAS Clara I, et al. Comparison of the immobilization of chiral bis(oxazoline)-copper complexes onto anionic solids and in ionic liquids[J]. Green Chemistry, 2004, 6(2): 93-98.
46	FRAILE José M, GARCı́A José I, HERRERı́AS Clara I, et al. Enantioselective cyclopropanation reactions in ionic liquids[J]. Tetrahedron: Asymmetry, 2001, 12(13): 1891-1894.
47	DAVIES David L, KANDOLA Sukhvinder K, PATEL Raj K. Asymmetric cyclopropanation in ionic liquids: Effect of anion and impurities[J]. Tetrahedron: Asymmetry, 2004, 15(1): 77-80.
48	GARCÍA José I, Beatriz LÓPEZ-SÁNCHEZ, MAYORAL José A, et al. Surface confinement effects in enantioselective catalysis: Design of new heterogeneous chiral catalysts based on C₁-symmetric bisoxazolines and their application in cyclopropanation reactions[J]. Journal of Catalysis, 2008, 258(2): 378-385.
49	CORNEJO Alfonso, FRAILE José M, GARCı́A José I, et al. Surface-mediated improvement of enantioselectivity with clay-immobilized copper catalysts[J]. Journal of Molecular Catalysis A: Chemical, 2003, 196(1/2): 101-108.
50	孙伟, 夏春谷, 王爱勤. 壳聚糖希夫碱铜多相催化剂催化苯乙烯环丙烷化反应研究[J]. 化学学报, 2002, 60(1): 162-165, 13.
	SUN Wei, XIA Chungu, WANG Aiqin. Cyclopropanation of styrene catalyzed by chitosan Schiff-base copper (Ⅰ) heterogeneous catalyst [J]. Acta Chimica Sinica, 2002, 60(1):162-165, 13.
51	CABALLERO Ana, SABATER Mariano, Esther MORILLA M, et al. Hydrotrispyrazolylborate-copper complexes as catalysts for the styrene cyclopropanation reaction with ethyl diazoacetate under homogeneous and heterogeneous conditions[J]. Inorganica Chimica Acta, 2009, 362(12): 4599-4602.
52	SYUKRI Syukri, FISCHER Christian E, HMAIDEEN Akef AL, et al. Modified MCM-41-supported acetonitrile ligated copper(Ⅱ) and its catalytic activity in cyclopropanation of olefins [J]. Microporous and Mesoporous Materials, 2008, 113(1): 171-177.
53	SYUKRI Syukri, HIJAZI Ahmed K, SAKTHIVEL Ayyamperumal, et al. Heterogenization of solvent-ligated copper(Ⅱ) complexes on poly(4-vinylpyridine) for the catalytic cyclopropanation of olefins[J]. Inorganica Chimica Acta, 2007, 360(1): 197-202.
54	SAKTHIVEL Ayyamperumal, SYUKRI S, HIJAZI Ahmed K, et al. Heterogenization of [Cu(NCCH₃)₄][BF₄]₂ on mesoporous AlMCM-41/AlMCM-48 and its application as cyclopropanation catalyst[J]. Catalysis Letters, 2006, 111(1/2): 43-49.
55	CASTANO Brunilde, ZARDI Paolo, HÖNEMANN Yvonne C, et al. Silica “SHB” chiral Pc-L* copper complexes for halogen-free solvent cyclopropanation reactions [J]. RSC Advances, 2013, 3(44): 22199-22205.
56	朱新举, 牛俊龙, 赵雪梅, 等. 联苯骨架手性双咪唑啉配体的合成及在不对称环丙烷化中的应用[J]. 有机化学, 2018, 38(1): 118-123.
	ZHU Xinju, NIU Junlong, ZHAO Xuemei, et al. Synthesis of chiral bis(imidazoline) ligands with biphenyl backbone and their application in the asymmetric cyclopropanation reaction[J]. Chinese Journal of Organic Chemistry, 2018, 38(1): 118-123.
57	Lorenz RÖSLER, HÖFLER Mark V, BREITZKE Hergen, et al. Dirhodium complex immobilization on modified cellulose for highly selective heterogeneous cyclopropanation reactions[J]. Cellulose, 2022, 29(11): 6283-6299.
58	DAVIES Huw M L, WALJI Abbas M, NAGASHIMA Tadamichi. Simple strategy for the immobilization of dirhodium tetraprolinate catalysts using a pyridine-linked solid support[J]. Journal of the American Chemical Society, 2004, 126(13): 4271-4280.
59	GUTMANN Torsten, LIU Jiquan, ROTHERMEL Niels, et al. Natural abundance ¹⁵N NMR by dynamic nuclear polarization: Fast analysis of binding sites of a novel amine-carboxyl-linked immobilized dirhodium catalyst[J]. Chemistry-A Europen Journal, 2015, 21(9): 3798-3805.
60	LIU Jiquan, GROSZEWICZ Pedro B, WEN Qingbo, et al. Revealing structure reactivity relationships in heterogenized dirhodium catalysts by solid-state NMR techniques[J]. The Journal of Physical Chemistry C, 2017, 121(32): 17409-17416.
61	LI Zhenzhong, Lorenz RÖSLER, WISSEL Till, et al. Immobilization of a chiral dirhodium catalyst on SBA-15 via click-chemistry: Application in the asymmetric cyclopropanation of 3-diazooxindole with aryl alkenes[J]. Journal of CO₂ Utilization, 2021, 52: 101682.
62	Jiquan LIU , PLOG Andreas, GROSZEWICZ Pedro, et al. Design of a heterogeneous catalyst based on cellulose nanocrystals for cyclopropanation: Synthesis and solid-state NMR characterization[J]. Chemistry-A European Journal, 2015, 21(35): 12414-12420.
63	LEVCHENKO Vladimir, Bård SUNDSLI, Sigurd ØIEN-ØDEGAARD, et al. Bottom-up synthesis of acrylic and styrylic Rh^Ⅱ carboxylate polymer beads: Solid-supported analogs of Rh₂(OAc)₄ [J]. European Journal of Organic Chemistry, 2018, 2018(44): 6150-6157.
64	ALCÓN M J, CORMA A, IGLESIAS Marta, et al. From homogeneous to heterogeneous catalysis: zeolite supported metal complexes with C2-multidentate nitrogen ligands. Application as catalysts for olefin hydrogenation and cyclopropanation reactions[J]. Journal of Organometallic Chemistry, 2002, 655(1/2): 134-145.
65	CIAMMAICHELLA Alina, CARDONI Valeria, LEONI Aessandro, et al. Rhodium porphyrin bound to a Merrifield resin as heterogeneous catalyst for the cyclopropanation reaction of olefins[J]. Molecules, 2016, 21(3): 278.
66	GILL Christopher S, VENKATASUBBAIAH Krishnan, JONES Christopher W. Recyclable polymer- and silica-supported ruthenium(Ⅱ)-salen bis-pyridine catalysts for the asymmetric cyclopropanation of olefins[J]. Advanced Synthesis & Catalysis, 2009, 351(9): 1344-1354.
67	ZHANG Junlong, LIU Yunling, CHE Chiming. Chiral ruthenium porphyrin encapsulated in ordered mesoporous molecular sieves (MCM-41 and MCM-48) as catalysts for asymmetric alkene epoxidation and cyclopropanation[J]. Chemical Communications, 2002(23): 2906-2907.
68	CASELLI Alessandro, BUONOMENNA Maria Giovanna, DE BALDIRONI Federico, et al. From homogeneously to heterogeneously catalyzed cyclopropanation reactions: New polymeric membranes embedding cobalt chiral schiff base complexes[J]. Journal of Molecular Catalysis A: Chemical, 2010, 317(1/2): 72-80.
69	CORMA Avelino, IGLESIAS Marta, LIABRÉS I XAMENA Francesc X, et al. Cu and Au metal-organic frameworks bridge the gap between homogeneous and heterogeneous catalysts for alkene cyclopropanation reactions[J]. Chemistry-A European Journal, 2010, 16(32): 9789-9795.
70	HEINZ Werner R, JUNK Raphael, Iker AGIRREZABAL-TELLERIA, et al. Thermal defect engineering of precious group metal–organic frameworks: impact on the catalytic cyclopropanation reaction[J]. Catalysis Science & Technology, 2020, 10(23): 8077-8085.
71	SHI Fanian, SILVA Ana Rosa, ROCHA João. Metal-organic framework based on copper(Ⅰ) sulfate and 4,4'-bipyridine catalyzes the cyclopropanation of styrene[J]. Journal of Solid State Chemistry, 2011, 184(8): 2196-2203.
72	Konstantin EPP, BUEKEN Bart, HOFMANN Benjamin J, et al. Network topology and cavity confinement-controlled diastereoselectivity in cyclopropanation reactions catalyzed by porphyrin-based MOFs[J]. Catalysis Science & Technology, 2019, 9(22): 6452-6459.
73	STEENHAUT Timothy, Nicolas GRÉGOIRE, Gabriella BAROZZINO-CONSIGLIO, et al. Mechanochemical defect engineering of HKUST-1 and impact of the resulting defects on carbon dioxide sorption and catalytic cyclopropanation[J]. RSC Advances, 2020, 10(34): 19822-19831.
74	FAN Zhiying, WANG Junjun, WANG Weijia, et al. Defect engineering of copper paddlewheel-based metal-organic frameworks of type NOTT-100: Implementing truncated linkers and its effect on catalytic properties[J]. ACS Applied Materials & Interfaces, 2020, 12(34): 37993-38002.

[1]	时永兴, 林刚, 孙晓航, 蒋韦庚, 乔大伟, 颜彬航. 二氧化碳加氢制甲醇过程中铜基催化剂活性位点研究进展[J]. 化工进展, 2023, 42(S1): 287-298.
[2]	高雨飞, 鲁金凤. 非均相催化臭氧氧化作用机理研究进展[J]. 化工进展, 2023, 42(S1): 430-438.
[3]	王乐乐, 杨万荣, 姚燕, 刘涛, 何川, 刘逍, 苏胜, 孔凡海, 朱仓海, 向军. SCR脱硝催化剂掺废特性及性能影响[J]. 化工进展, 2023, 42(S1): 489-497.
[4]	赵景超, 谭明. 表面活性剂对电渗析减量化工业含盐废水的影响[J]. 化工进展, 2023, 42(S1): 529-535.
[5]	王谨航, 何勇, 史伶俐, 龙臻, 梁德青. 气体水合物阻聚剂研究进展[J]. 化工进展, 2023, 42(9): 4587-4602.
[6]	林晓鹏, 肖友华, 管奕琛, 鲁晓东, 宗文杰, 傅深渊. 离子聚合物-金属复合材料（IPMC）柔性电极的研究进展[J]. 化工进展, 2023, 42(9): 4770-4782.
[7]	史天茜, 石永辉, 武新颖, 张益豪, 秦哲, 赵春霞, 路达. Fe²⁺对厌氧氨氧化EGSB反应器运行性能的影响[J]. 化工进展, 2023, 42(9): 5003-5010.
[8]	张丽宏, 金要茹, 程芳琴. 煤气化渣资源化利用[J]. 化工进展, 2023, 42(8): 4447-4457.
[9]	毛善俊, 王哲, 王勇. 基团辨识加氢：从概念到应用[J]. 化工进展, 2023, 42(8): 3917-3922.
[10]	向阳, 黄寻, 魏子栋. 电催化有机合成反应的活性和选择性调控研究进展[J]. 化工进展, 2023, 42(8): 4005-4014.
[11]	陈俊俊, 费昌恩, 段金汤, 顾雪萍, 冯连芳, 张才亮. 高生物活性聚醚醚酮化学改性研究进展[J]. 化工进展, 2023, 42(8): 4015-4028.
[12]	张耀杰, 张传祥, 孙悦, 曾会会, 贾建波, 蒋振东. 煤基石墨烯量子点在超级电容器中的应用[J]. 化工进展, 2023, 42(8): 4340-4350.
[13]	杨鹏威, 于琳竹, 王放放, 蒋昊轩, 赵光金, 李琦, 杜铭哲, 马双忱. 氨储能在新型电力系统的应用前景、挑战及发展[J]. 化工进展, 2023, 42(8): 4432-4446.
[14]	于姗, 段元刚, 张怡欣, 唐春, 付梦瑶, 黄靖元, 周莹. 分步法分解硫化氢制氢和硫黄催化剂研究进展[J]. 化工进展, 2023, 42(7): 3780-3790.
[15]	杨扬, 孙志高, 李翠敏, 李娟, 黄海峰. 静态条件下表面活性剂OP-13促进HCFC-141b水合物生成[J]. 化工进展, 2023, 42(6): 2854-2859.