含膦负载催化剂的合成及应用研究进展

doi:10.6023/cjoc202403016

摘要/Abstract

可回收使用的含膦负载型催化剂是当前绿色有机化学研究的热点之一, 在过去的十几年中, 含膦负载催化剂被广泛应用于各种有机反应中, 如C—C偶联、C—N偶联、氢化、氧化以及氢甲酰化等反应. 与均相催化剂相比, 含膦负载催化剂仍处于探索起步阶段, 非均相催化剂中P原子的电子性质还有待进一步研究. 主要对含膦的负载型催化剂进行归纳整理, 按照含膦负载催化剂不同的载体形式进行分类, 综述了含膦负载催化剂的合成及应用研究进展.

关键词: 含膦催化剂, 非均相催化, 负载型催化剂, 绿色化学

The recycled supported catalyst is one of the hot topics in green organic chemistry research. In the past decade, supported catalysts containing phosphine have been widely used in various organic reactions, such as C—C coupling, C—N coupling, hydrogenation, oxidation, and hydroformylation. Compared with homogeneous catalysts, supported catalysts containing phosphine are still in the early stages of exploration and development, and the electronic properties of P atoms in non-homogeneous catalysts need to be further investigated. In this review, the supported catalysts containing phosphine are summarized and classified according to the different carrier or support materials used, and then the latest progress in the synthesis and application of supported catalysts containing phosphine is reviewed.

Key words: phosphine-containing catalyst, heterogeneous catalysis, supported catalyst, green chemistry

引用此文

赵永哲, 孔翔飞, 张俊良, 杨俊锋. 含膦负载催化剂的合成及应用研究进展[J]. 有机化学, 2024, 44(12): 3587-3608.

Yongzhe Zhao, Xiangfei Kong, Junliang Zhang, Junfeng Yang. Research Progress in the Application of Supported Catalysts Containing Phosphine[J]. Chinese Journal of Organic Chemistry, 2024, 44(12): 3587-3608.

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图/表 29

图式1. 聚苯乙烯负载手性磷酸多相催化剂催化氢化反应

Scheme 1. Polystyrene-supported chiral phosphoric acid heterogeneous catalyst catalyzes hydrogenation

图式2. 聚苯乙烯负载醚功能化的膦配体的制备及催化应用

Scheme 2. Synthesis and catalytic application of polyether-functionalized phosphine ligands supported by polystyrene

图式3. 乙烯基功能化双膦配体聚合物的制备及催化氢甲酰化反应

Scheme 3. Preparation and catalytic hydroformylation of vinyl functionalized bisphosphine ligand polymers

图式4. Xantphos Rh/POPs-PPh3的制备及催化氢甲酰化反应

Scheme 4. Xantphos Rh/POPs-PPh3 synthesis and catalytic hydroformylation reaction

图式5. Rh/POL-BPa&PPh3的制备及催化氢甲酰化反应

Scheme 5. Rh/POL-BPa&PPh3 synthesis and catalytic hydroformylation reaction

图式6. 聚苯乙烯负载dppm、Xantphos的制备及催化反应

Scheme 6. Preparation and catalytic reactions of dppm and Xantphos supported by polystyrene

图式7. Pd/POL-dppe的制备及催化内炔硅氢化反应

Scheme 7. Preparation of Pd/POL-dppe and catalysis of internal acetylene hydrosilylation

图式8. Pd/Cu@POP-POPh3的制备及催化炔氧化反应

Scheme 8. Preparation of Pd/Cu@POP-POPh3 and catalytic oxidation of acetylene

图式9. 聚苯乙烯负载Sadphos/Pd催化不对称环加成和还原Heck反应

Scheme 9. Polystyrene supported Sadphos/Pd catalyzes asymmetric cycloaddition and reduction Heck reactions

图式10. 苯与三苯基膦Friedel-Crafts聚合

Scheme 10. Benzene and triphenylphosphine Friedel-Crafts polymerization

图式11. 钳形钌配合物通过“编织”策略制备多相催化剂

Scheme 11. Multiphase catalysts were prepared from clamped ruthenium complexes by a “direct knitting” strategy

图式12. 金、钌配合物通过“编织”策略合成多相催化剂及其应用

Scheme 12. Synthesis of heterogeneous catalysts by "direct knitting" strategy of gold and ruthenium complexes and their applications

图式13. 偶联反应

Scheme 13. Coupling reaction

图式14. Ru/BINAP-CMP-3D-2的制备及催化不对称氢化反应

Scheme 14. Preparation and catalytic asymmetric hydrogenation of Ru/BINAP-CMP-3D-2

图式15. Suzuki-Miyaura偶联聚合

Scheme 15. Suzuki-Miyaura coupling polymerization

图式16. Heck偶联聚合

Scheme 16. Heck coupling polymerization

图式17. Pd NPs@POL-2的制备及催化加氢反应

Scheme 17. Preparation and catalytic hydrogenation of Pd NPs@POL-2

图式18. P-COF的制备及催化应用

Scheme 18. Preparation and catalytic application of P-COF

图式19. 一锅法制备[Pd]@COF及催化反应

Scheme 19. Preparation of [Pd]@COF by one-pot method and catalytic reaction

图式20. Pd@PKOP的制备及催化内炔烃的双碳官能化反应

Scheme 20. Preparation of Pd@PKOP and the catalytic double carbon functionalization of intranyne

图式21. Cell-OPPh2-Pd0的制备及催化Heck偶联反应

Scheme 21. Preparation of Cell-OPPh2-Pd0 and catalysis of Heck coupling reaction

图式22. 纤维素负载钯多相催化剂的制备及催化Suzuki-Miyaura偶联反应

Scheme 22. Preparation and catalytic Suzuki-Miyaura coupling of cellulose-supported palladium heterogeneous catalysts

图式23. Cell-OOCPhPPh2-Pd的制备及催化偶联反应

Scheme 23. Preparation and catalytic coupling reaction of Cell-OOCPhPPh2-Pd

图式24. Cell-OPPh2-Cu(II)的制备及催化偶联反应

Scheme 24. Preparation and catalytic coupling reaction of Cell-OPPh2-Cu(II)

图式25. DAC-BINAP-Rh的制备及不对称催化加氢反应

Scheme 25. Preparation and asymmetric catalytic hydrogenation of DAC-BINAP-Rh

图式26. Chitosan-Rh的制备及催化氢甲酰化反应

Scheme 26. Preparation and catalytic hydroformylation reaction of Chitosan-Rh

图式27. SiO2负载钯催化剂的制备及催化Suzuki-Miyaura偶联反应

Scheme 27. Preparation and catalytic Suzuki-Miyaura coupling reaction of SiO2-supported palladium catalyst

图式28. SiO2@Fe3O4-Pd的制备及催化Hiyama反应

Scheme 28. Preparation and catalysis of Hiyama reaction by SiO2@Fe3O4-Pd

图式29. Fe3O4@SiO2@PPh2@Pd0的制备及催化反应

Scheme 29. Preparation and catalytic reaction of Fe3O4@SiO2@PPh2@Pd0

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