Research Progress of Cellulose and Its Derivatives Supported Copper Catalyst Catalyzed Organic Reactions

doi:10.6023/cjoc202007063

Abstract

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

Cite this article

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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Fig. & Tab. 43

Figure1. Molecular structure of cellulose

Figure 2. Some important cellulose and its derivatives

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 13. Synthesis of the cellulose-supported copper nanoparticles

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

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

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

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

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

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

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

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

Scheme 22. Dendrocalamus giganteus Munro functionalized Cu-LμR

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

Scheme 24. Grafting of phthalocyanine on crystalline nanocellulose

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

Scheme 26. Formation of CuS hollow nanospheres

Scheme 27. Mechanism of CIP adsorption and catalytic oxidation

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

Scheme 29. Preparation of CCMs

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

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

Scheme 32. Preparation of Fe/Cu@MCC

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

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

Figure 3. Common organic dyes

Scheme 35. Mechanism of dye degradation process

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

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

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

Scheme 39. Proposed mechanism for the decarboxylation reactions

Scheme 40. Proposed reaction pathway of decarboxylative nitration reaction

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