纤维素及其衍生物负载铜催化有机反应的研究进展

doi:10.6023/cjoc202007063

摘要/Abstract

纤维素作为自然界中含量最丰富的天然聚合物, 存在于高等植物、棉花、藻类和细菌等各种物质中, 并且被科研工作者作为金属纳米粒子的负载材料用于有机合成和催化的研究中. 近代以来, 过渡金属催化领域发展迅猛, 但由于存在着成本高、分离难以及不可回收再利用等缺点, 所以越来越多的科研工作者利用纤维素及其衍生物负载过渡金属, 实现非均相催化. 从经济高效的角度来看, 纤维素及其衍生物负载廉价金属铜粒子, 不仅可以高效地参与各种类型的有机转化, 还能多次循环、再生利用, 解决了均相催化剂的诸多弊端, 实现绿色化学. 以不同类型纤维素铜催化剂的制备途径为线索, 对其催化的有机反应进行了综述, 主要涉及C—X键的构建、环加成、氧化、还原、光催化降解和电催化等反应类型, 为今后纤维素及其衍生物催化剂的广泛应用起到推动作用.

关键词: 纤维素负载铜催化剂, 功能化纤维素, 合成制备, 有机反应, 非均相催化

Cellulose, the most abundant natural polymer in nature, is found in vascular plant, cotton, algae and bacteria, and it can be widely employed in organic synthesis and catalytic chemistry as a loading material for metal nanoparticles. In modern times, the field of transition metal catalysis has been developed rapidly, but it has the disadvantages of high cost, difficulty of separation and non-recyclable reuse, thus more and more researchers use cellulose and its derivatives to carry out heterogeneous catalysis. From an economic and efficient point of view, cheap cellulose and its derivatives-loaded copper particles can not only participate in various types of organic conversion efficiently, but also can be recycled and reused many times, thus solving many disadvantages of homogeneous catalysts and achieving green process. The organic reactions catalyzed by different types of cellulose-supported copper catalysts are reviewed, including the construction of C—X bond, cycloaddition, oxidation, reduction, photocatalytic degradation and electrocatalysis. It will promote the application of cellulose and its derivatives-sup- ported catalysts in the future.

Key words: cellulose-supported copper catalyst, functional cellulose, synthesis, organic reaction, heterogeneous catalysis

引用此文

陈鑫, 陈春霞, 彭进松. 纤维素及其衍生物负载铜催化有机反应的研究进展[J]. 有机化学, 2021, 41(4): 1319-1336.

Xin Chen, Chunxia Chen, Jinsong Peng. Research Progress of Cellulose and Its Derivatives Supported Copper Catalyst Catalyzed Organic Reactions[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1319-1336.

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图/表 43

图1. 纤维素中的分子结构

Figure1. Molecular structure of cellulose

图2. 一些重要的纤维素及其衍生物

Figure 2. Some important cellulose and its derivatives

图式1. 咪唑与芳基硼酸和芳基卤化物进行N-芳基化反应

Scheme 1. N-Arylation of imidazole with aryl halides and arylboronic acids

图式2. α,β-不饱和化合物的Aza-Michael反应

Scheme 2. Aza-Michael reaction of α,β-unsaturated carbonyl compounds

图式3. 合成查尔酮的Claisen-Schmidt缩合反应

Scheme 3. Claisen-Schmidt condensation reaction for synthesis of chalcone

图式4. 废玉米芯纤维素负载的CuN@PA的合成

Scheme 4. Synthesis of waste corn-cob cellulose-supported CuN@PA

图式5. A3偶联反应及CMC-Cu(II)催化剂的制备

Scheme 5. A3-coupling reaction and the preparation of CMC- Cu(II) catalyst

图式6. CMC-Cu(II)参与的A3偶联反应机理

Scheme 6. Proposed reaction mechanism for the A3-coupling involving CMC-Cu(II)

图式7. CMC-Cu(II)参与的C—C偶联反应机理

Scheme 7. Proposed reaction mechanism for the C—C coupling involving CMC-Cu(II)

图式8. CuI/Fe3O4NPs@IL-g-Cs催化剂的制备

Scheme 8. Preparation of CuI/Fe3O4NPs@IL-g-Cs catalyst

图式9. CuI/Fe3O4NPs@Lg-Cs催化合成N-磺酰脒和N-磺酰基丙烯基脒

Scheme 9. CuI/Fe3O4NPs@IL-g-Cs catalyzed synthesis of N-sulfonylamidines and N-sulfonylacrylamidines

图式10. 三组分反应合成磺酰脒类衍生物

Scheme 10. Three-component synthesis of N-sulfonylformami- dines

图式11. γ-Fe2O3/Cu@Cellulose催化二氢吡啶和多氢喹啉的合成

Scheme 11. Synthesis of dihydropyridines and polyhydroquinolines using γ-Fe 2O3/Cu@Cellulose as a catalyst

图式12. 二氢吡啶和多氢喹啉的合成机理

Scheme 12. Proposed mechanism for the synthesis of dihydropyridine and polyhydroquinoline derivatives

图式13. 纳晶纤维素负载的铜纳米粒子的合成

Scheme 13. Synthesis of the cellulose-supported copper nanoparticles

图式14. 丙烯酸甲酯和哌啶之间的C—N偶联反应的机理图

Scheme 14. Mechanistic view of the C—N coupling reaction between methyl acrylate and piperidine

图式15. 细菌纳米纤维素(BNC)负载铜纳米颗粒

Scheme 15. Bacterial nanocellulose (BNC)-supported copper nanoparticles

图式16. TOCNs上负载Cu(I)离子和Huisgen [3+2]环加成反应

Scheme 16. Topological loading of Cu(I) ions on crystalline TOCNs and Huisgen [3+2] cycloaddition

图式17. Cell-Cu(I)催化合成1,2,3-三唑的机理

Scheme 17. Mechanism of cell-Cu(I) catalysed synthesis of 1,2,3-triazoles

图式18. NHC-Cu/CL的制备示意图

Scheme 18. Schematic description for the preparation of NHC-Cu/CL

图式19. (A) Cell-Cu(0)催化糖基叠氮化物和末端炔烃的环加成及(B)阿拉伯吡喃基叠氮化物和(C)吡喃葡萄糖基叠氮化物的合成

Scheme 19. (A) Cellulose-Cu(0) catalyzed the cycloaddition of glycosyl azides and terminal alkynes, (B) synthesis of arabinopyranosylazide and (C) glucopyranosyl azide

图式20. Cu(I)/Cell-SH催化Huisgen [3+2]环加成反应

Scheme 20. Cu(I)/Cell-SH catalyzed Huisgen [3+2] cycloaddition reaction

图式21. 洋麻纤维素负载的CuN@PHA的制备

Scheme 21. Preparation of Kenaf bio-cellulose-supported CuN@PHA

图式22. 龙竹功能化Cu-LμR

Scheme 22. Dendrocalamus giganteus Munro functionalized Cu-LμR

图式23. Cell/Cu的制备及催化点击反应

Scheme 23. Preparation of Cell/Cu and catalyzed click reaction

图式24. 酞菁改性纳米晶纤维素

Scheme 24. Grafting of phthalocyanine on crystalline nanocellulose

图式25. 四氨基和四硫代酞菁功能化纤维素的制备

Scheme 25. Preparation of functionalized cellulose with tetra-amino and tetra-thiophthalocyanine

图式26. CuS空心纳米球的形成

Scheme 26. Formation of CuS hollow nanospheres

图式27. CIP的吸附机理图和催化氧化机理图

Scheme 27. Mechanism of CIP adsorption and catalytic oxidation

图式28. CNs作为CuO NPs的负载材料和稳定剂的示意图

Scheme 28. Schematic illustration using CNs as supporting materials and stabilizer for CuO NPs

图式29. CCMs的制备

Scheme 29. Preparation of CCMs

图式30. 4-NP转化为4-AP的机理图

Scheme 30. Mechanism for the conversion of 4-NP to 4-AP

图式31. Cu NPs@CMC/PAM的制备及4-NP的还原反应

Scheme 31. Preparation of Cu NPs@CMC/PAM and the reduction of 4-NP

图式32. Fe/Cu@MCC的制备

Scheme 32. Preparation of Fe/Cu@MCC

图式33. Fe3O4@SiO2@Cellulose@poly-GMA@EDA纳米复合物的制备

Scheme 33. Preparation of Fe3O4@SiO2@Cellulose@poly- GMA@EDA nanocomposite system

图式34. HMF催化转移加氢合成BHMF示意图

Scheme 34. Schematic representation for the catalytic transfer hydrogenation of HMF to BHMF

图3. 常见的有机染料

Figure 3. Common organic dyes

图式35. 染料降解过程的机理示意图

Scheme 35. Mechanism of dye degradation process

图式36. Fe3O4@CNC/Cu/GSPE表面的文拉法辛可能发生的电氧化机理

Scheme 36. Electrooxidation mechanisms for venlafaxine at the surface of Fe3O4@CNC/Cu/GSPE

图式37. Cell-Cu(0)脱肟的可能机理

Scheme 37. A plausible mechanism for the deoximation using Cell-Cu(0)

图式38. Cell-Cu(0)催化的脱羧反应

Scheme 38. Decarboxylation for the catalysis of cell-Cu(0)

图式39. 脱羧反应机理

Scheme 39. Proposed mechanism for the decarboxylation reactions

图式40. 脱羧硝化可能的机理

Scheme 40. Proposed reaction pathway of decarboxylative nitration reaction

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