Research Progress of Chitosan Supported Copper Catalyst in Organic Reactions

doi:10.6023/cjoc202107066

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (1): 33-53.DOI: 10.6023/cjoc202107066 Previous Articles Next Articles

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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

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)

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

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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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Fig. & Tab. 37

Figure 1. The structure of chitosan (CS)

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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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