木质素及其衍生物负载金属催化剂在有机合成中的应用研究进展
收稿日期: 2022-08-19
修回日期: 2022-09-21
网络出版日期: 2022-11-15
基金资助
中央高校基本科研业务费专项(2572020AW45); 黑龙江省自然科学基金(ZD2021C001); 高等学校学科创新引智计划(B20088)
Research Progress in Application of Lignin and Its Derivatives Supported Metal Catalysts in Organic Synthesis
Received date: 2022-08-19
Revised date: 2022-09-21
Online published: 2022-11-15
Supported by
Fundamental Research Funds for the Central Universities(2572020AW45); Natural Science Foundation of Heilongjiang Province(ZD2021C001); Program of Introducing Talents of Discipline to Universities(B20088)
碳中和发展理念的提出使得生物质基催化剂的关注度不断提高, 将木质素作为过渡金属催化剂的载体来制备非均相催化剂应用于有机合成领域, 可以极大地提高木质素的利用价值. 木质素结构中广泛存在的含氧官能团为金属催化剂的负载提供了多种结合位点, 通过物理吸附/沉积、离子交换以及与羟基官能团通过静电络合可以有效地捕获金属粒子. 首先介绍了木质素的结构, 然后介绍了制备非均相催化剂的方法, 重点介绍了木质素及其衍生物负载金属催化剂催化点击反应、Glaser反应、Huisgen [3＋2]环加成反应、Heck反应、Suzuki反应、Sonogashira反应、Stille偶联反应、迈克尔加成/脱水串联反应、亲电开环反应、Fridel-Crafts型反应及乙烯聚合反应等, 并对存在的问题和发展趋势进行了展望.
关键词： 功能化木质素; 木质素负载金属催化剂; 非均相催化; 有机合成; 绿色化学
莫百川 , 陈春霞 , 彭进松 . 木质素及其衍生物负载金属催化剂在有机合成中的应用研究进展[J]. 有机化学, 2023 , 43(4) : 1215 -1240 . DOI: 10.6023/cjoc202207013
The attention of biomass-based catalysts has been continuously increased due to the proposal of carbon neutralization development concept. The use of lignin as a support for transition metal catalysts for the preparation of heterogeneous catalysts in the field of organic synthesis can greatly improve the utilization value of lignin. The extensive presence of oxygen-containing functionalities in the lignin structure provides a variety of binding sites for the loading of metal catalysts, and metal particles can be efficiently captured by physical adsorption/deposition, ion exchange, and electrostatic complexation with hydroxyl functional groups. The structure of lignin is firstly introduced, and the methods for preparing heterogeneous catalysts are then described. Lignin and its derivatives supported metal catalysts catalyzed Click reaction, Glaser reaction, Huisgen [3＋2] cycloaddition reaction, Heck reaction, Suzuki reaction, Sonogashira reaction, Stille coupling, Michael addition/dehydration tandem, Electrophilic ring-opening reaction, Fridel-Crafts type reaction, ethylene polymerization and other reactions. Thus, at the end of this review, the existing problems and development trends are prospected.
| [1] | Schulze, F. Chem. Zentralbl. 1857, 21, 321. |
| [2] | Adler, E. Wood Sci. Technol. 1977, 11, 169. |
| [3] | Pan, X. J.; Kadla, J. F.; Ehara, K.; Gilkes, N.; Saddler, J. N. J. Agric. Food Chem. 2006, 54, 5806. |
| [4] | Liew, R. K.; Nam, W. L.; Chong, M. Y.; Phang, X. Y.; Su, M. H.; Yek, P. N. Y.; Ma, N. L.; Cheng, C. K.; Chong, C. T.; Lam, S. S. Process Saf. Environ. Prot. 2018, 115, 57. |
| [5] | Anderson, E. M.; Katahira, R.; Reed, M.; Resch, M. G.; Karp, E. M.; Beckham, G. T. ACS Sustainable Chem. Eng. 2016, 4, 6940. |
| [6] | Gioia, C.; Re, L. G.; Lawoko, M.; Berglund, L. J. Am. Chem. Soc. 2018, 140, 4054. |
| [7] | Pu, Y. Q.; Cao, S. L.; Ragauskas, A. J. Energy Environ. Sci. 2011, 4, 3154. |
| [8] | Freudenberg, K. Nature 1959, 183, 1152. |
| [9] | Zakzeski, J.; Bruijnincx, P. C. A.; Jongerius, A. L.; Weckhuysen, B. M. Chem. Rev. 2010, 110, 3552. |
| [10] | Wang, Y. P.; Dai, L. L.; Fan, L. L.; Shan, S. Q.; Liu, Y. H.; Roger, R. J. Anal. Appl. Pyrolysis 2016, 119, 104. |
| [11] | Wang, C.; Kelley, S. S.; Venditti, R. A. ChemSusChem 2016, 9, 770. |
| [12] | Ralph, J.; Lundquist, K.; Brunow, G.; Lu, F. C.; Kim, H.; Schatz1, P. F.; Marita, J. M.; Hatfield, R. D.; Ralph, S. A.; Christensen, J. H.; Boerjan,, W. Phytochem. Rev. 2004, 3, 29. |
| [13] | Boeriu, C. G.; Bravo, D.; Gosselink, R. J. A.; Dam, J. E. G. V. Ind. Crops Prod. 2004, 20, 205. |
| [14] | Chakar, F. S.; Ragauskas, A. J. Ind. Crops Prod. 2004, 20. 131. |
| [15] | Wikberg, H.; Ohra-aho, T.; Pileidis, F.; Titirici, M. M. ACS Sustainable Chem. Eng. 2015, 3, 2737. |
| [16] | Río, J. C. D.; Rencoret, J.; Marques, G.; Gutiérrez, A.; Ibarra, D.; Santos, J. I.; Jiménez-Barbero, J.; Zhang, L. M.; Martínez, á. T. J. Agric. Food Chem. 2008, 56, 9525. |
| [17] | Zakzeski, J.; Bruijnincx, P. C. A.; Jongerius, A. L.; Weckhuysen, B. M. Chem. Rev. 2010, 110, 3552. |
| [18] | Vanholme, R.; Morreel, K.; Ralph, J.; Boerjan, W. Curr. Opin. Plant Biol. 2008, 11, 278. |
| [19] | Nada, A. A. M. A.; El-sakhawy, M.; Kamel, S. Int. J. Polym. Mater. Polym. Biomater. 2000, 46, 121. |
| [20] | Boerjan, W.; Ralph, J.; Baucher, M. Annu. Rev. Plant Biol. 2003, 54, 519. |
| [21] | Hatakeyama, H.; Hatakeyama, T. Adv. Polym. Sci. 2010, 232, 1. |
| [22] | Li, C. Z.; Zhao, X. C.; Wang, A. Q.; Huber, G. W.; Zhang, T. Chem. Rev. 2015, 115, 11559. |
| [23] | Kai, D.; Tan, M. J.; Chee, P. L.; Chua, Y. K.; Yap, Y. L.; Loh X. J. ; Green Chem. 2016, 18, 1175. |
| [24] | Saito, T.; Brown, R. H.; Hunt, M. A.; Pickel, D. L.; Pickel, J. M.; Messman, J. M.; Baker, F. S.; Keller, M.; Naskar, A. K. Green Chem. 2012, 14, 3295. |
| [25] | Culebras, M.; Geaney, H.; Beaucamp, A.; Upadhyaya, P.; Dalton E. Ryan, K. M.; Collins, M. N. ChemSusChem 2019, 12, 4516. |
| [26] | Sun, S. H.; Bai, R. X.; Gu, Y. L. Chem.-Eur. J. 2014, 20, 549. |
| [27] | Lai, B. B.; Bai, R. X.; Gu, Y. L. ACS Sustainable Chem. Eng. 2018, 6, 17076. |
| [28] | Zhou, Z. D.; Peng, X. W.; Zhong, L. X.; Li, X. H.; Sun, R. C. Polymers 2018, 10, 724. |
| [29] | Wang, Y. L.; Ren, K.; Sun, J.; Li, W.; Zhao, S. L.; Chen, Z. H.; Guan, J. G. Compos. Sci. Technol. 2017, 140, 89. |
| [30] | Lu, C.; Qi, L.; Yang, J.; Wang, X.; Zhang, D.; Xie, J.; Ma, J. Adv. Mater. 2005, 17, 2562. |
| [31] | Lai, B. B.; Ye, M.; Liu, P.; Li, M. H.; Bai, R. X.; Gu, Y. L. Beilstein J. Org. Chem. 2020, 16, 2888. |
| [32] | Akhtar, K.; Ali, F.; Sohni, S.; Kamal, T.; Asiri, A. M.; Bakhsh, E. M.; Khan, S. B. Environ. Sci. Pollut. Res. 2020, 27, 823. |
| [33] | Ahmadpoor, F.; Nasrollahzadeh, M.; Mohammad, M. Sep. Purif. Technol. 2021, 272, 118864. |
| [34] | Huang, Y. J.; Kang, Y.; El-kott, A.; Ahmed, A. E.; Khames, A.; Zein, M. A. Arabian J. Chem. 2021, 14, 103299. |
| [35] | Nasrollahzadeh, M.; Soleimani, F.; Nezafat, Z.; Orooji, Y.; Ah-madpoor, F. Biomass Conv. Bioref. 2021, 12, 1. |
| [36] | Nasrollahzadeh, M.; Bidgoli, N. S. S.; Karimkhani, M. M. Biomass Convers. Biorefin. 2021, https://doi.org/10.1007/s13399-021-01841-y. |
| [37] | Chanda, D.; Tufa, R. A.; Aili, D.; Basu, S. Nanotechnology 2022, 33, 055403. |
| [38] | Mohami, R.; Shakeri, A.; Nasrollahzadeh, M. Sep. Purif. Technol. 2022, 285, 120373. |
| [39] | Wu, Y. F.; Cui, Y. C. J. Mol. Catal. 2008, 6, 526. (in Chinese) |
| [39] | (吴玉锋, 崔元臣, 分子催化, 2008, 6, 526.) |
| [40] | Guillén, E.; Rico, R.; López-Romero, J. M.; Bedia, J.; Rosas, J. M.; Rodríguez-Mirasol, J.; Cordero, T. Appl. Catal., A 2009, 368, 113. |
| [41] | Wu, Y. F.; Zhang, L.; Cui, Y. C.; Liu, J. S.; Yang, S. Petrochem. Technol. 2009, 38, 733. (in Chinese) |
| [41] | (吴玉锋, 张磊, 崔元臣, 刘降生, 杨帅, 石油化工, 2009, 38, 733.) |
| [42] | Xue, M.; Zhang, S. Z.; Wu, Y. F.; Liu, J.; Cui, Y. C. Chin. J. Appl. Chem. 2010, 27, 787. (in Chinese) |
| [42] | (薛蔓, 张士真, 吴玉锋, 刘剑, 崔元臣, 应用化学, 2010, 27, 787.) |
| [43] | Coccia, F.; Tonucci, L.; d'Alessandro, N.; D'Ambrosio, P.; Bressan, M. Inorg. Chim. Acta 2013, 399, 12. |
| [44] | Marulasiddeshwara, M. B.; Kumar, P. R. Int. J. Biol. Macromol. 2016, 83, 326. |
| [45] | Marulasiddeshwara, M. B.; Kumar, P. R. Mater. Today: Proc. 2018, 5, 20811. |
| [46] | Nasrollahzadeh, M.; Issaabadi, Z.; Varma, R. S. ACS Omega 2019, 4, 14234. |
| [47] | Chao, M.; Zhang, G. W.; Li, Z. Y.; Liu, L. H.; Yan, S. Q.; Chen, Y.; Shi, Y. H.; Yan, X.; Cao, C. S. ChemistrySelect 2019, 4, 766. |
| [48] | Nasrollahzadeh, M.; Bidgoli, N. S. S.; Issaabadi, Z.; Ghavamifar, Z.; Baran, T.; Luque, R. Int. J. Biol. Macromol. 2020, 148, 265. |
| [49] | Bharamanagowda, M. M.; Panchangam, R. K. Appl. Organomet. Chem. 2020, 34, 5837. |
| [50] | Baran, T.; Sargin, I. Int. J. Biol. Macromol. 2020, 155, 814. |
| [51] | Chen, S. L.; Wang, G. H.; Sui, W. J.; Parvez, A. M.; Dai, L.; Si, C. L. Ind. Crops Prod. 2020, 145, 112164. |
| [52] | Orooji, Y.; Pakzad, K.; Nasrollahzadeh, M.; Tajbakhsh, M. Int. J. Biol. Macromol. 2021, 182, 564. |
| [53] | Ji, T.; Chen, L.; Schmitz, M.; Bao, F. S.; Zhu, J. H. Green Chem. 2015, 17, 2515. |
| [54] | Gao, C.; Wang, X. L.; Zhai, S. R.; An, Q. D. Int. J. Biol. Macromol. 2019, 134, 202. |
| [55] | Gao, C.; Wang, X. L.; Wang, H. S.; Zhou, J. H.; Zhai, S. R.; An, Q. D. Int. J. Biol. Macromol. 2020, 144, 947. |
| [56] | Chen, S. L.; Wang, G. H.; Pang, T. R.; Sui, W. J.; Chen, Z. C.; Si, C. L. Int. J. Biol. Macromol. 2021, 166, 893. |
| [57] | Yang, J.; Liu, L. Q.; An, X. Y.; Seta, F. T.; Li, C. X.; Zhang, H.; Luo, B. Y.; Hu, Q.; Zhang, R. Q.; Nie, S. X.; Cao, H. B.; Cheng, Z. B.; Liu, H. B. Ind. Crops Prod. 2021, 169, 113644. |
| [58] | Zazo, J. A.; Bedia, J.; Fierro, C. M.; Pliego, G.; Casas, J. A.; Rodriguez, J. J. Catal. Today 2012, 187, 115. |
| [59] | Yan, Q. G.; Wan, C. X.; Liu, J.; Gao, J. S.; Yu, F.; Zhang, J. L.; Cai, Z. Y. Green Chem. 2013, 15, 1631. |
| [60] | Chieffi, G.; Fechler, N.; Esposito, D. RSC Adv. 2015, 5, 63691. |
| [61] | Song, K. P.; Tang, C.; Zou, Z. J.; Wu, Y. D. Transition Met. Chem. 2020, 45, 111. |
| [62] | Chen, X. Y.; Yuan, B.; Yu, F. L.; Liu, Y. X.; Xie, C. X.; Yu, S. T. ACS Omega 2020, 5, 8902. |
| [63] | Zhang, J. R.; Yao, R. X.; Chen, J. Z.; Li, T.; Xu, Y. S. iScience 2021, 24, 103045. |
| [64] | Wang, S. W.; Feng, N.; Zheng, J. L.; Yoon, K. B.; Lee, D.; Qu, M. J.; Zhang, X. Q.; Zhang, H. X. Polym. Adv. Technol. 2016, 27, 1351. |
| [65] | Zhang, X. P.; Lu, G. P.; Wang, K.; Lin, Y. M.; Wang, P. C.; Yi, W. B. Nano Res. 2022, 15, 1874. |
| [66] | Zhu, Y. C.; Wu, H.; Fang, Z.; Yang, X. B.; Guo, K.; He, W. Mol. Catal. 2021, 514, 111765. |
| [67] | Chen, D. W.; Liang, F. B.; Feng, D. X.; Du, F. L.; Zhao, G.; Liu, H. Z.; Xian, M. Catal. Commun. 2016, 84, 159. |
| [68] | Zimmerman, J. B.; Anastas, P. T.; Erythropel, H. C.; Leitener, W. Science 2020, 367, 397. |
/
| 〈 |
|
〉 |
