Chinese Journal of Organic Chemistry >
Research Progress in the Application of Supported Catalysts Containing Phosphine
Received date: 2024-03-12
Revised date: 2024-05-01
Online published: 2024-05-17
Supported by
National Key Research and Development Program of China(2021YFF0701600); National Natural Science Foundation of China(22271053); National Natural Science Foundation of China(22031004); National Natural Science Foundation of China(21921003); Science and Technology Commission of Shanghai Municipality(21ZR1445900); Shanghai Municipal Education Commission(20212308)
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.
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 . DOI: 10.6023/cjoc202403016
| [1] | (a) Shaghaleh H.; Xu X.; Wang S. RSC Adv. 2018, 8, 825. |
| [1] | (b) Guibal E. Prog. Polym. Sci. 2005, 30, 71. |
| [1] | (c) Macquarrie D. J.; Hardy J. J. E. Ind. Eng. Chem. Res. 2005, 44, 8499. |
| [2] | (a) Lang R.; Li T.-B.; Matsumura D.; Miao S.; Ren Y.-J.; Cui Y.-T.; Tan Y.; Qiao B.-T.; Li L.; Wang A.-Q.; Wang X.-D.; Zhang T. Angew. Chem., Int. Ed. 2016, 55, 16054. |
| [2] | (b) Kontkanen M.; Tuikka M.; Kinnunen N. M.; Suvanto S.; Haukka M. Catalysts 2013, 3, 324. |
| [2] | (c) Bergonia H. A.; Phillips J. D.; Kushner J. P. Anal. Biochem. 2009, 384, 74. |
| [3] | (a) Kumar P.; Das A.; Maji B. Org. Biomol. Chem. 2021, 19, 4174. |
| [3] | (b) G?umann P.; Cartagenova D.; Ranocchiari M. Eur. J. Org. Chem. 2022, 48, e202201006. |
| [3] | (c) Shinde P. S.; Suryawanshi P. S.; Patil K. K.; Belekar V. M.; Sankpal S. A.; Delekar S. D.; Jadhav S. A. J. Compos. Sci. 2021, 3, 75. |
| [4] | Rueping M.; Sugiono E.; Steck A.; Theissmann T. Adv. Synth. Catal. 2010, 352, 281. |
| [5] | Parrish C. A.; Buchwald S. L. J. Org. Chem. 2001, 66, 3820. |
| [6] | Yu H.-W.; Guan M.; Tong Q.-S.; Jia L.; Jin Z.-L.; Shi J.-C. Chin. J. Org. Chem. 2011, 31, 1100 (in Chinese). |
| [6] | (于宏伟, 官旻, 童庆松, 贾莉, 金子林, 施继成, 有机化学, 2011, 31, 1100.) |
| [7] | Sun Q.; Dai Z.-F.; Liu X.-L.; Sheng N.; Deng F.; Meng X.-J.; Xiao F.-S. J. Am. Chem. Soc. 2015, 137, 5204. |
| [8] | Li C.-Y.; Sun K.-J.; Wang W.-L.; Yan L.; Sun X.-P.; Wang Y.-Q.; Xiong K.; Zhan Z.-P.; Jiang Z.; Ding Y.-J. J. Catal. 2017, 353, 123. |
| [9] | Jia X.-F.; Liang Z.-Y.; Chen J.-B.; Lv J.-H.; Zhang K.; Gao M.-J.; Zong L.-B.; Xie C.-X. Org. Lett. 2019, 21, 2147. |
| [10] | Pan Y.-M.; Wang H.-S.; Tang H.-T. Org. Lett. 2018, 20, 2494. |
| [11] | Pan Y.-M.; Tang H.-T.; Huang K.-B. Org. Lett. 2019, 21, 4929. |
| [12] | Ren S.-C.; Ye B.-C.; Li S.-Y.; Pang L.-P.; Pan Y.-M.; Tang H.-T. Nano. Res. 2022, 2, 1500. |
| [13] | Song J.-X.; Zhang K.; Huang Z.-Y.; Zhao J.-Y.; Yang Z.-Y.; Zong L.-B.; Chen J.-B.; Xie C.-X.; Jia X.-F. Catal. Sci. Technol. 2022, 12, 722. |
| [14] | (a) Zhang P.-C.; Li Y.-L.; He J.-F.; Wu H.-H.; Li Z.-M.; Zhang J.-L. Nat. Commun. 2021, 12, 4609. |
| [14] | (b) Zhao G.-F.; Wu Y.; Wu H.-H.; Yang J.-F.; Zhang J.-L. J. Am. Chem. Soc. 2021, 143, 17983. |
| [14] | (c) Luo W.-J.; Zhang L.-M.; Zhang Z.-M.; Zhang J.-L. Angew. Chem., Int. Ed. 2022, 61, e202204443. |
| [14] | (d) Han J.; Liu S.-Y.; Wang H.-N.; Wang J.; Qian H.; Li Z.-M.; Ma S.-M.; Zhang J.-L. Sci. Adv. 2023, 9, eadg1002. |
| [15] | Chen M.-J.; Zhang Z.-M.; Yu Z.-Z.; Qiu H.-L.; Ma B.; Wu H.-H.; Zhang J.-L. ACS Catal. 2015, 5, 7488. |
| [16] | Zhang H.; Xu B.; Zhou L.-J.; Zhang Z.-M.; Zhang J.-L. Green Synth. Catal. 2024, 2, 102. |
| [17] | Li B.-Y.; Guan Z.-H.; Wang W.; Yang X.-J.; Hu J.-L.; Tan B.-E.; Li T. Adv. Mater. 2012, 24, 3390. |
| [18] | Guan Z.-H.; Li B.-Y.; Hai G.-L.; Yang X.-J.; Li T.; Tan B.-E. RSC. Adv. 2014, 4, 36437. |
| [19] | Wang X.-B.; Min S.-X.; Das S. K.; Fan W.; Huang K.-W.; Lai Z.-P. J. Catal. 2017, 355, 101. |
| [20] | Wang X.-B.; Ling E. A. P.; Guan C.; Zhang Q.-G.; Wu W.-T.; Liu P.-X.; Zheng N.-F.; Zhang D.-L.; Lopatin S.; Lai Z.-P.; Huang K.-W. Chem. Sus. Chem. 2018, 11, 3591. |
| [21] | Wen D.-H.; Chen J.-B.; Zheng Q.-S.; Yang S.-Q.; Tu T. CCS Chem. 2023, 5, 1602. |
| [22] | Yang Y.-T.; Wang T.-N.; Jing X.-F.; Zhu G.-S. J. Mater. Chem. A 2019, 7, 10004. |
| [23] | Valverde-González A.; Marchal G.; Maya E. M.; Iglesias M. Catal. Sci. Technol. 2019, 9, 4552. |
| [24] | Xu Y.-H.; Jin S.-B.; Xu H.; Nagai A.; Jiang D.-L. Chem. Soc. Rev. 2013, 42, 8012. |
| [25] | Wang X.; Lu S.-M.; Li J.; Liu Y.; Li C. Catal. Sci. Technol. 2015, 5, 2585. |
| [26] | Chen J.; Zhang J.; Zhu D.-J.; Li T. J. Porous. Mater. 2017, 24, 847. |
| [27] | Jiang X.-Y.; Zhao W.-X.; Wang W.; Zhang F.; Zhuang X.-D.; Han S.; Feng X.-L. Polym. Chem. 2015, 6, 6351. |
| [28] | Ding Z.-C.; Li C.-Y.; Chen J.-J.; Zeng J.-H.; Tang H.-T.; Ding Y.-J.; Zhan Z.-P. Adv. Synth. Catal. 2017, 359, 2280. |
| [29] | Diercks C. S.; Yaghi O. M. Science 2017, 355, eaal1585. |
| [30] | Tao R.; Shen X.-R.; Hu Y.-M.; Kang K.; Zheng Y.-Q.; Luo S.-C.; Yang S.-Y.; Li W.-L.; Lu S.-L.; Jin Y.-H.; Qiu L.; Zhang W. Small 2020, 16, 1906005. |
| [31] | Liu Y.-B.; Dikhtiarenko A.; Xu N.-Z.; Sun J.-W.; Tang J.; Wang K.-Q.; Xu B.-L.; Tong Q.; Heeres H. J.; He S.-B.; Gascon J.; Fan Y.-N. Chem. Eur. J. 2020, 26, 12134. |
| [32] | Yang X.; Du Y.-R.; Guan P.-X.; Liu H.-Y.; Wang Y.-F.; Xu B.-H. ChemCatChem 2022, 14, e202101594. |
| [33] | Kumar P.; Maji B. J. Mater. Chem. A 2023, 11, 20752. |
| [34] | Qiu X.-Y.; Hu S.-W. Materials 2013, 6, 738. |
| [35] | Du Q.-W.; Li Y.-Q. Res. Chem. Intermed. 2012, 38, 1807. |
| [36] | Wang X.-X.; Hu P.-B.; Wei Y.-P. Chemistry Bioengineering 2014, 7, 37 (in Chinese). |
| [36] | (王晓霞, 胡培博, 魏玉萍, 化学与生物工程, 2014, 7, 37.) |
| [37] | Wang X.-X.; Xu Y.-J.; Wang F.; Wei Y.-P. J. Appl. Polym. Sci. 2015, 132, 41427. |
| [38] | Lu Z.-C.; Jasinski J. B.; Handa S.; Hammond G. B. Org. Biomol. Chem. 2018, 16, 2748. |
| [39] | Chen X.; Mo B.-C.; Bian Y.-Y.; Li X.; Shi L.-X.; Peng J.-S.; Chen C.-X. Fine Chemicals 2022, 39, 1 (in Chinese). |
| [39] | (陈鑫, 莫百川, 边芸芸, 李雪, 施连旭, 彭进松, 陈春霞, 精细化工, 2022, 39, 1.) |
| [40] | Yu C.-P.; Wu W.-L.; Gao M.; Liu Y. Catalysts 2022, 12, 83. |
| [41] | Adler E. Wood Sci. Technol. 1977, 11, 169. |
| [42] | Guillen E.; Rico R.; Lopez-Romero J. M.; Bedia J.; Rosas J. M.; Rodr?guez-Mirasol J.; Cordero T. Appl. Catal. A 2009, 368, 113. |
| [43] | Zhang J.-R.; Yao R.-X.; Chen J.-Z.; Li T.; Xu Y.-S. iScience 2021, 24, 103045. |
| [44] | Demetgül C. Carbohydr. Polym. 2012, 89, 354. |
| [45] | Makhubela B. C. E.; Jardine A.; Smith G. S. Green. Chem. 2012, 14, 338. |
| [46] | (a) Polshettiwar V.; Lenb C.; Coord A. F. Coord. Chem. Rev. 2009, 253, 2599. |
| [46] | (b) Jin R.-H.; Zheng D.-S.; Liu R.; Liu G.-H. ChemCatChem 2018, 10, 1739. |
| [47] | Li X.-M.; Ding Y.-J.; Jiao G.-P.; Li J.-W.; Yan L.; Zhu H.-J. J. Nat. Gas Chem. 2008, 17, 351. |
| [48] | Li X.-M.; Ding Y.-J.; Jiao G.-P.; Li J.-W.; Yan L.; Zhu H.-J. Chem. Res. Chin. Univ. 2009, 5, 738. |
| [49] | Liu J.; Yan L.; Jiang M.; Li C.-Y.; Ding Y.-J. Chin. J. Catal. 2016, 37, 268. |
| [50] | Sudheesh N.; Chaturvedi A. K.; Shukla R. S. Appl. Catal. A 2011, 409-410, 99. |
| [51] | Chen W.; Li P.-H.; Wang L. Tetrahedron 2011, 67, 318. |
| [52] | Mohammed A. T. A.; Wang L.-J.; Jin R.-H.; Liu G.-H.; Tan C.-X. Catalysts 2021, 11, 582. |
| [53] | (a) Polshettiwar V.; Luque R.; Fihri A.; Zhu H.; Bouhrara M.; Basset J. M. Chem. Rev. 2011, 111, 3036. |
| [53] | (b) Polshettiwar V.; Varma R. S. Green. Chem. 2010, 12, 743. |
| [54] | Zhang L.; Li P.-H.; Li H.-J.; Wang L. Catal. Sci. Technol. 2012, 2, 1859. |
| [55] | Li P.-H.; Wang L.; Zhang L.; Wan G.-W. Adv. Synth. Catal. 2012, 354, 1307. |
| [56] | Zolfigol M. A.; Khakyzadeh V.; Moosavi-Zare A. R.; Rostami A.; Zare A.; Iranpoor N.; Beyzavie M. H.; Luquef R. Green. Chem. 2013, 15, 2132. |
/
| 〈 |
|
〉 |