壳聚糖负载铜催化剂在有机反应中的应用研究进展

doi:10.6023/cjoc202107066

有机化学 ›› 2022, Vol. 42 ›› Issue (1): 33-53.DOI: 10.6023/cjoc202107066 上一篇下一篇

综述与进展

壳聚糖负载铜催化剂在有机反应中的应用研究进展

张瑶瑶^a^,^*(), 周丽洁^a^,^b, 韩彪^a^,^b, 李维双^a, 李博解^a^,^*(), 朱磊^a^,^b^,^c^,^*()

a 湖北工程学院化学与材料科学学院湖北孝感 432000
b 湖北大学材料科学与工程学院武汉 430062
c 华中科技大学生物无机化学与药物湖北省重点实验室武汉 430074

收稿日期:2021-07-31 修回日期:2021-09-11 发布日期:2021-09-26
通讯作者: 张瑶瑶, 李博解, 朱磊
基金资助:
国家自然科学基金(21774029); 国家自然科学基金(22108065); 湖北省自然科学基金(2019CFB354); 湖北省高等学校优秀中青年科技创新团队计划(T201816); 孝感市自然科学计划(XGKJ2020010053); 孝感市自然科学计划(XGKJ2021010009)

Research Progress of Chitosan Supported Copper Catalyst in Organic Reactions

Yaoyao Zhang^a(), Lijie Zhou^a^,^b, Biao Han^a^,^b, Weishuang Li^a, Bojie Li^a(), Lei Zhu^a^,^b^,^c()

a School of Chemistry and Materials Science, Hubei Engineering University, Xiaogan, Hubei 432000
b School of Materials Science and Engineering, Hubei University, Wuhan 430062
c Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, Huazhong University of Science and Technology, Wuhan 430074

Received:2021-07-31 Revised:2021-09-11 Published:2021-09-26
Contact: Yaoyao Zhang, Bojie Li, Lei Zhu
Supported by:
National Natural Science Foundation of China(21774029); National Natural Science Foundation of China(22108065); Natural Science Foundation of Hubei Province(2019CFB354); Young and Middle-Aged Science and Technology Innovation Team Project in Higher Education Institutions of Hubei Province(T201816); Natural Science Foundation of Xiaogan City(XGKJ2020010053); Natural Science Foundation of Xiaogan City(XGKJ2021010009)

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摘要/Abstract

壳聚糖是由甲壳素脱乙酰化而得, 是一种丰富可再生的生物质资源. 壳聚糖分子结构中含有大量的羟基、氨基, 与金属纳米粒子或金属离子具有较强的鳌合能力, 被广泛用作载体制备异相催化剂. 近年来, 壳聚糖负载铜催化剂被成功应用于各种不同类型的有机反应中, 不仅具有反应活性高、选择性好、易于分离回收等优点, 而且能够多次循环再利用, 在降低反应成本的同时, 也提升了实际的工业应用价值. 因此, 从不同类型壳聚糖负载铜催化剂的制备出发, 综述其催化的各种类型的有机反应, 主要涉及C—C键和C—X键的构建、点击化学及氧化还原反应等类型, 促进今后壳聚糖及其衍生物负载催化剂更加广泛的应用.

关键词: 壳聚糖负载铜催化剂, 有机反应, 异相催化, 绿色化学, 循环再利用

Chitosan is obtained by deacetylation of chitin and is a kind of abundant renewable biomass resource. The molecular structure of chitosan contains a large number of hydroxyl and amino groups, which have strong bonding ability with metal nanoparticles or metal ions. Thus it has been widely used to support various metal particles for the preparation of catalysts. In recent years, chitosan supported copper catalyst has been successfully applied in various types of organic reactions. It has the advantages of high reactivity, good selectivity, easy separation, and can also be reused for many times, which reduces the reaction cost and improves the actual industrial application value. Therefore, based on the preparation of different types of chitosan supported copper catalysts, various types of organic reactions are reviewed, mainly involving the constructions of C—C bond and C—X bond, click chemistry and oxidation/reduction reactions. It will promote the application of chitosan and its derivatives-supported catalysts in the future.

Key words: chitosan supported copper catalyst, organic reaction, heterogeneous catalysis, green chemistry, recycle and reuse

引用此文

张瑶瑶, 周丽洁, 韩彪, 李维双, 李博解, 朱磊. 壳聚糖负载铜催化剂在有机反应中的应用研究进展[J]. 有机化学, 2022, 42(1): 33-53.

Yaoyao Zhang, Lijie Zhou, Biao Han, Weishuang Li, Bojie Li, Lei Zhu. Research Progress of Chitosan Supported Copper Catalyst in Organic Reactions[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 33-53.

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图/表 37

图1. 壳聚糖分子结构

Figure 1. The structure of chitosan (CS)

图式1. 壳聚糖-席夫碱铜(C1~C4)催化烯烃的环丙烷化反应

Scheme 1. Cyclopropanation of styrene by chitosan-Schiff base copper catalysts (C1~C4)

图式2. PCMS@CuI (C5)催化Heck反应可能机理

Scheme 2. Proposed mechanism of PCMS@CuI (C5) catalyzed Heck reaction

图式3. CS@Cu(OAc)2 (C6)催化的8-氨基喹啉酰胺的三氟甲基化反应

Scheme 3. Trifluoromethylation of 8-aminoquinoline amides catalyzed by CS@Cu(OAc)2 (C6)

图式4. C7催化不同醛和β-二羰基化合物合成不同的1,4-DHP衍生物

Scheme 4. C7 catalyzed synthesis of different 1,4-DHP derivatives from different aldehydes and β-dicarbonyl compounds

图式5. 催化剂C8的结构及末端炔烃氧化偶联

Scheme 5. Structure of C8 and oxidative homo-coupling of terminal alkynes

图式6. 壳聚糖衍生物C9和C10合成路线及Henry反应

Scheme 6. Synthesis route of chitosan derivatives C9 and C10 and catalyzed for Henry (nitroaldol) reaction

图式7. CS@CuI (C11)催化A3/脱羧A3偶联反应及可能机理

Scheme 7. CS@CuI (C11) catalyzed A3/decarboxylative A3- coupling reaction and proposed reaction mechanism

图式8. MMT/CS@Pd0/Cu2+(C12)催化芳族卤化物与炔烃的Sonogashira交叉偶联反应

Scheme 8. MMT/CS@Pd0/Cu2+(C12) catalyzed Sonogashira cross-coupling of aromatic halides with alkynes

图式9. 二胺与氨基醇的偶联反应

Scheme 9. C—N cross coupling between aryl halides and aliphatic diamines

图式10. 壳聚糖锚定铜席夫碱(C14~C16)的制备及催化胺的N-芳基化

Scheme 10. Preparation of chitosan anchored copper(II) Schiff base complexes (C13~C15) and catalyzed N-arylation of amines

图式11. 催化剂CSP@CuO的结构及其催化卤代芳烃与苯胺偶联反应

Scheme 11. Coupling reactions of aryl halides with aniline and structure of CSP@CuO

图式12. PCCS@CuI (C18)催化的C—N偶联反应

Scheme 12. PCCS@CuI (C18) catalyzed C—N coupling reaction

图式13. 催化剂C21的制备及催化C—N偶联反应

Scheme 13. Preparation of C21 and catalyzed C—N coupling reaction

图式14. CS@Tet-IL-Cu(II) (C22)催化合成芳基胺四氮唑

Scheme 14. Schematic representation of synthesis of arylaminotetrazoles using CS@Tet-IL-Cu(II) (C22)

图式15. CS@Cu(OAc)2 (C25)催化卤代芳烃与亚硫酸钠的 C—S偶联反应

Scheme 15. CS@Cu(OAc)2 (C25) catalyzed C—S cross-coupling between aryl halides and sodium sulfinates

图式16. CS@Cu NPs (C26)催化硫酚和芳基卤化物的C—S偶联反应

Scheme 16. CS@Cu NPs (C26) catalyzed C—S cross-couplings between thiophenol and aryl halides

图式17. 催化剂his/CS@Cu(II)(C27)的制备及催化合成芳基苄基硫醚

Scheme 17. Preparation of his/CS@Cu(II) (C27) and catalyzed to synthesis of aryl benzyl sulfides

图式18. 催化剂C28的制备路径及其应用于合成芳基苄基硫醚

Scheme 18. Preparation of C28 and application of synthesis aryl benzyl sulfides

图式19. CS@CuI (C29)催化的合成异喹啉N-氧化物磺酸酯

Scheme 19. CS@CuI (C29) catalyzed synthesis of sulfonate esters of isoquinoline N-oxides

图式20. C30于水相中催化α,β-不饱和受体的硼化反应

Scheme 20. C30 catalyzed borylation of α,β-unsaturated acceptors in water

图式21. 复合薄膜负载铜C31催化α,β-不饱和受体的硼化反应

Scheme 21. Composite film loaded with copper C31 catalyzed borylation of α,β-unsaturated acceptors

图式22. C32 催化α,β-不饱和受体的共轭硅烷化

Scheme 22. C32 catalyzed conjugate silylation of α,β-unsaturated acceptors

图式23. C42催化Huisgen[3+2]环加成反应

Scheme 23. C42 catalyzed Huisgen [3+2] cycloaddition

图式24. 交联的CS@Cu(I) (C44)催化合成三唑

Scheme 24. Synthesis of triazole catalyzed by cross-linked CS@Cu(I) (C44)

图式25. CS@CuSO4 (C45)催化叠氮苄与苯乙炔的偶极环加成反应

Scheme 25. CS@CuSO4 (C45) catalyzed dipolar cycloaddition of benzyl azide and phenyl acetylene

图式26. CS-AAPTS@CuBr (C46)催化合成1,2,3-三唑

Scheme 26. CS-AAPTS@CuBr (C46) catalyzed synthesis of 1,2,3-trazoles

图式27. CS/Fe3O4@Cu (C47)催化叠氮-炔环加成反应

Scheme 27. CS/Fe3O4@Cu (C47) catalyzed azide-alkyne cycloaddition

图式28. CS@CuSO4 (C48)在水中催化合成1,4-二取代-1,2,3-三唑

Scheme 28. Synthesis of 1,4-disubstituted-1,2,3-triazolesusing using C48 as catalyst in water

图式29. 磁性壳聚糖铜/凝胶纳米复合材料C49催化卤化物与末端炔烃的环加成反应

Scheme 29. Cycloaddition of alkyl halides with terminal alkynes in the presence of CuII-magnetic chitosan nanocomposite C49

图式30. CS@CuBP (C50)催化的叠氮烷基环加成

Scheme 30. CS@CuBP (C50) catalyzed azide-alkyne cycloaddition

图式31. 壳聚糖负载salen Cu配合物型催化剂C51结构

Scheme 31. Structure of chitosan supported Salen Cu complex catalyst C51

图式32. Fe3O4/CS@Cu (C52)催化硫醚氧化反应

Scheme 32. Fe3O4/CS@Cu (C52) catalyzed sulfur oxidation reaction

图式33. Schiff-Fe3O4/CS@Cu (C53)催化硫醚氧化反应

Scheme 33. Schiff-Fe3O4/CS@Cu (C53) catalyzed sulfur oxidation reaction

图式34. 壳聚糖/聚乙烯醇膜负载铜(C54)催化还原硝基苯

Scheme 34. Catalytic reduction of NB to AN in the presence of NaBH4 by C54

图式35. 在催化剂C55存在下NaBH4还原硝基苯酚的可能机理

Scheme 35. Proposed mechanism for the reduction of nitrophenol by NaBH4 in the presence of C55

图式36. CS@Cu2O纳米粒子存在下对硝基苯酚的光还原和电还原实例

Scheme 36. Illustration of photoreduction and electroreduction of p-nitrophenol reduction with the present of CS@Cu2O nanoparticles

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壳聚糖负载铜催化剂在有机反应中的应用研究进展

Research Progress of Chitosan Supported Copper Catalyst in Organic Reactions

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