Chinese Journal of Organic Chemistry >
Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis
Received date: 2023-06-12
Revised date: 2023-08-14
Online published: 2023-08-30
Supported by
National Natural Science Foundation of China(21865040); National Natural Science Foundation of China(22005356); Guizhou Provincial Science and Technology Program(QKHPTRC[2019]1463); Science and Technology Department of Zunyi(ZSKRPT-2020-5); Science and Technology Department of Zunyi(ZSKH-2018-3); Science and Technology Department of Zunyi(ZSKRPT-2021-5); Graduate Research Foundation of Zunyi Medical University(ZYK82)
Carbon nanotubes (CNTs), graphite oxide (GO), graphene (G), activated carbon (AC), and materials generated by AC after doping or modification are examples of carbon-based metal-free catalysts. These catalysts are used in critical chemical processes like energy conversion. Due to its advantages of abundant materials, low cost, environmental friendliness, straightforward post-processing and sustainable development, carbon-based metal-free catalysts have been successfully used in the field of organic synthesis in recent years. The application of carbon-based metal-free catalysts in oxidation, reduction, substitution and coupling reactions has been successfully reported. However, the research on the active site of carbon-based metal-free catalysts used in organic synthesis is still in its early stage of development. Recent research has mostly concentrated on the characterization and study of catalysts as well as first-principles predictions for their mechanisms, but generally consistent experimental conclusions have not been reached. Therefore, the application and mechanism research of carbon-based metal-free catalysts in the field of organic synthesis are reviewed.
Qianfan Zhao , Yongzheng Chen , Shiming Zhang . Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2024 , 44(1) : 137 -147 . DOI: 10.6023/cjoc202306010
| [1] | Ge, S.; Liu, X.; Liu, J.; Liu, H.; Liu, H.; Chen, X.; Wang, G.; Chen, J.; Zhang, G.; Zhang, Y.; Li, J. Fuel 2022, 314, 123061. |
| [2] | Wan, L.; Miao, S.; He, Z.; Li, X.; Zhou, X.; Gao, F. ACS Omega 2021, 6, 23347. |
| [3] | Shen, X.; Yang, J.; Zhang, J.; Jiang, H.; Du, Y.; Chen, R. Ind. Eng. Chem. Res. 2023, 62, 279. |
| [4] | Yu, Z.; Li, Y.; Torres-Pinto, A.; LaGrow, A. P.; Diaconescu, V. M.; Simonelli, L.; Sampaio, M. J.; Bondarchuk, O.; Amorim, I.; Araujo, A.; Silva, A. M. T.; Silva, C. G.; Faria, J. L.; Liu, L. Appl. Catal., B: Environ. 2022, 310, 121318. |
| [5] | Ge, M.; Zhang, X.; Xia, S.; Luo, W.; Jin, Y.; Chen, Q.; Nie, H.; Yang, Z. Chin. J. Chem. 2021, 39, 2113. |
| [6] | Hu, X.; Guo, F.; Zhu, R.; Zhou, B.; Zhang, T.; Fang, L. Chin. J. Org. Chem. 2023, 43, 2239 (in Chinses). |
| [6] | (户晓兢, 郭斐翔, 朱润青, 周柄棋, 张涛, 房立真, 有机化学, 2023, 43, 2239.) |
| [7] | Maurer, F.; Beck, A.; Jelic, J.; Wang, W.; Mangold, S.; Stehle, M.; Wang, D.; Dolcet, P.; G?nzler, A. M.; Kübel, C.; Studt, F.; Casapu, M.; Grunwaldt, J.-D. ACS Catal. 2022, 12, 2473. |
| [8] | Mohammadi, A.; Farzi, A.; Thurner, C.; Kl?tzer, B.; Schwarz, S.; Bernardi, J.; Niaei, A.; Penner, S. Appl. Catal., B: Environ. 2022, 307, 121160. |
| [9] | Ai, X.; Chen, H.; Liang, X.; Shi, L.; Zhang, M.; Zhang, K.; Zou, Y.; Zou, X. ACS Catal. 2022, 12, 2967. |
| [10] | Pang, S.; Liu, F.; Zhang, Y.; Dong, Z.; Su, Q.; Wang, W.; Li, Z.; Zhou, F.; Wang, Y. ACS Sustainable Chem. Eng. 2021, 9, 9062. |
| [11] | Zheng, P.; Jiang, W.; Qin, Q.; Li, D. Molecules (Basel, Switzerland) 2021, 26, 5199. |
| [12] | Modekwe, H. U.; Mamo, M.; Moothi, K.; Daramola, M. O. Mater. Today: Proc. 2021, 38, 549. |
| [13] | Jiang, J.; Zheng, X.; Meng, Y.; He, W.; Chen, Y.; Zhuang, Q.; Yuan, J.; Ju, Z.; Zhang, X. Acta Chim. Sinica 2023, 81, 319 (in Chinese). |
| [13] | (蒋江民, 郑欣冉, 孟雅婷, 贺文杰, 陈亚鑫, 庄全超, 袁加仁, 鞠治成, 张校刚, 化学学报, 2023, 81, 319.) |
| [14] | Choudhary, P.; Bahuguna, A.; Kumar, A.; Dhankhar, S. S.; Nagaraja, C. M.; Krishnan, V. Green Chem. 2020, 22, 5084. |
| [15] | Nosan, M.; Lffler, M.; Jerman, I.; Kolar, M.; Genorio, B. ACS Appl. Energy Mater. 2021, 4, 3593. |
| [16] | Zeng, Y.; Lyu, P.; Cai, Y.; Gao, F.; Zhuo, O.; Wu, Q.; Yang, L.; Wang, X.; Hu, Z. Acta Chim. Sinica. 2021, 79, 539 (in Chinese). |
| [16] | (曾誉, 吕品, 蔡跃进, 高福杰, 卓欧, 吴强, 杨立军, 王喜章, 胡征, 化学学报, 2021, 79, 539.) |
| [17] | Singla, S.; Sharma, S.; Basu, S.; Shetti, N. P.; Reddy, K. R. FlatChem. 2020, 24, 100200. |
| [18] | Yi, H.; Nakabayashi, K.; Yoon, S.-H.; Miyawaki, J. RSC Adv. 2022, 12, 2558. |
| [19] | Zhao, S.; Lu, X.; Wang, L.; Gale, J.; Amal, R. Adv. Mater. 2019, 31, 1805367. |
| [20] | Liu, D.; Dai, L.; Lin, X.; Chen, J.-F.; Zhang, J.; Feng, X.; Müllen, K.; Zhu, X.; Dai, S. Adv. Mater. 2019, 31, 1804863. |
| [21] | Zhao, S.; Wang, D.-W.; Amal, R.; Dai, L. Adv. Mater. 2019, 31, 1801526. |
| [22] | Ahmad, M. S.; Nishina, Y. Nanoscale. 2020, 12, 12210. |
| [23] | Messele, S. A.; Chelme-Ayala, P.; Gamal El-Din, M. Catal. Today. 2021, 361, 102. |
| [24] | Zhang, J.; Liu, X.; Blume, R.; Zhang, A.; Su, D. S. Science. 2008, 322, 73. |
| [25] | Jiang, T.; Jiang, W.; Li, Y.; Xu, Y.; Zhao, M.; Deng, M.; Wang, Y. Carbon 2021, 180, 92. |
| [26] | Mollar-Cuni, A.; Ventura-Espinosa, D.; Martín, S.; García, H.; Mata, J. A. ACS Catal. 2021, 11, 14688. |
| [27] | Teh, W. P.; Obenschain, D. C.; Black, B. M.; Michael, F. E. J. Am. Chem. Soc. 2020, 142, 16716. |
| [28] | Huang, T.; Fu, Y.; Peng, Q.; Yu, C.; Zhu, J.; Yu, A.; Wang, X. Appl. Surf. Sci. 2019, 480, 888. |
| [29] | Chen, S. S.; Carraher, J. M.; Tuci, G.; Rossin, A.; Raman, C. A.; Luconi, L.; Tsang, D. C. W.; Giambastiani, G.; Tessonnier, J.-P. ACS Sustainable Chem. Eng. 2019, 7, 16959. |
| [30] | Yuan, J.; Wang, Z.; Liu, J.; Li, J.; Chen, J. Environ. Sci. Technol. 2023, 57, 606. |
| [31] | Enders, L.; Casadio, D. S.; Aikonen, S.; Lenarda, A.; Wirtanen, T.; Hu, T.; Hietala, S.; Ribeiro, L. S.; Pereira, M. F. R.; Helaja, J. Catal. Sci. Technol. 2021, 11, 5962. |
| [32] | Anthore-Dalion, L.; Nicolas, E.; Cantat, T. ACS Catal. 2019, 9, 11563. |
| [33] | Yang, J.-H.; Sun, G.; Gao, Y.; Zhao, H.; Tang, P.; Tan, J.; Lu, A.-H.; Ma, D. Energy Environ. Sci. 2013, 6, 793. |
| [34] | Dhakshinamoorthy, A.; Primo, A.; Concepcion, P.; Alvaro, M.; Garcia, H. Chemistry 2013, 19, 7547. |
| [35] | Dreyer, D. R.; Jia, H.-P.; Todd, A. D.; Geng, J.; Bielawski, C. W. Org. Biomol. Chem. 2011, 9, 7292. |
| [36] | Zhang, J.; Chen, S.; Chen, F.; Xu, W.; Deng, G.-J.; Gong, H. Adv. Synth. Catal. 2017, 359, 2358. |
| [37] | Tanaka, T.; Okunaga, K.-i.; Hayashi, M. Tetrahedron Lett. 2010, 51, 4633. |
| [38] | Long, J.; Xie, X.; Xu, J.; Gu, Q.; Chen, L.; Wang, X. ACS Catal. 2012, 2, 622. |
| [39] | Grant, J. T.; Carrero, C. A.; Goeltl, F.; Venegas, J.; Mueller, P.; Burt, S. P.; Specht, S. E.; McDermott, W. P.; Chieregato, A.; Hermans, I. Science 2016, 354, 1570. |
| [40] | Rozanska, X.; Fortrie, R.; Sauer, J. J. Phys. Chem. C 2007, 111, 6041. |
| [41] | Grabow, L. C.; Mavrikakis, M. ACS Catal. 2011, 1, 365. |
| [42] | Hummers, W. S.; Offeman, R. E. J. Am. Chem. Soc. 1958, 80, 1334. |
| [43] | Li, D.; Müller, M. B.; Gilje, S.; Kaner, R. B.; Wallace, G. G. Nat. Nanotechnol. 2008, 3, 101. |
| [44] | Gao, Y.; Hu, G.; Zhong, J.; Shi, Z.; Zhu, Y.; Su, D. S.; Wang, J.; Bao, X.; Ma, D. Angew. Chem., Int. Ed. 2013, 52, 2109. |
| [45] | Zhu, Y.-N.; Cao, C.-Y.; Jiang, W.-J.; Yang, S.-L.; Hu, J.-S.; Song, W.-G.; Wan, L.-J. J. Mater. Chem. A. 2016, 4, 18470. |
| [46] | Hou, S.; Chen, N.; Zhang, P.; Dai, S. Green Chem. 2019, 21, 1455. |
| [47] | Vermeulen, L. A.; Thompson, M. E. Nature 1992, 358, 656. |
| [48] | Geim, A. K. Science 2009, 324, 1530. |
| [49] | Stankovich, S.; Dikin, D. A.; Dommett, G.; Kohlhaas, K. M.; Zimney, E. J.; Stach, E. A.; Piner, R. D.; Nguyen, S.; Ruoff, R. S. Nature 2006, 442, 282. |
| [50] | Dreyer, D. R.; Jia, H. P.; Bielawski, C. W. Angew. Chem., Int. Ed. 2010, 49, 6813. |
| [51] | Li, X.; Yuan, Z.; Liu, Y.; Yang, H.; Nie, J.; Wang, G.; Liu, B. ChemSusChem 2022, 15, 1. |
| [52] | Huang, J.; Bai, J.; Feng, J.; Jiang, Q.; Yang, G.; Wang, H.; Yu, H.; Zhang, Q.; Cao, Y.; Peng, F. ACS Sustainable Chem. Eng. 2022, 10, 6713. |
| [53] | Cai, Z.; Liu, D.; Huang, J.; Feng, J.; Wang, H.; Yang, G.; Peng, F.; Cao, Y.; Yu, H. Ind. Eng. Chem. Res. 2022, 61, 2037. |
| [54] | Gao, Y.; Ma, D.; Wang, C.; Guan, J.; Bao, X. Chem. Commun. 2011, 47, 2432. |
| [55] | Yang, F.; Chi, C.; Wang, C.; Wang, Y.; Li, Y. Green Chem. 2016, 18, 4254. |
| [56] | Wei, Q.; Qin, F.; Ma, Q.; Shen, W. Carbon 2019, 141, 542. |
| [57] | Wu, S.; Wen, G.; Wang, J.; Rong, J.; Zong, B.; Schl?gl, R.; Su, D. S. Catal. Sci. Technol. 2014, 4, 4183. |
| [58] | Choi, C. H.; Lim, H.-K.; Chung, M. W.; Park, J. C.; Shin, H.; Kim, H.; Woo, S. I. J. Am. Chem. Soc. 2014, 136, 9070. |
| [59] | Zhang, J.; Li, S.; Deng, G.-J.; Gong, H. ChemCatChem 2018, 10, 376. |
| [60] | Ghorpade, P. V.; Pethsangave, D. A.; Some, S.; Shankarling, G. S. J. Org. Chem. 2018, 83, 7388. |
| [61] | Rodrigo, E.; García Alcubilla, B.; Sainz, R.; Fierro, J. L. G.; Ferritto, R.; Cid, M. B. Chem. Commun. 2014, 50, 6270. |
| [62] | Primo, A.; Franconetti, A.; Magureanu, M.; Mandache, N. B.; Bucur, C.; Rizescu, C.; Cojocaru, B.; Parvulescu, V. I.; Garcia, H. Green Chem. 2018, 20, 2611. |
| [63] | Kawashita, Y.; Yanagi, J.; Fujii, T.; Hayashi, M. Bull. Chem. Soc. Jpn. 2009, 82, 482. |
| [64] | Hu, F.; Patel, M.; Luo, F.; Flach, C.; Mendelsohn, R.; Garfunkel, E.; He, H.; Szostak, M. J. Am. Chem. Soc. 2015, 137, 14473. |
| [65] | Meng, G.; Patel, M.; Luo, F.; Li, Q.; Flach, C.; Mendelsohn, R.; Garfunkel, E.; He, H.; Szostak, M. Chem. Commun. 2019, 55, 5379. |
| [66] | Zhang, J.; Yang, Y.; Fang, J.; Deng, G. J.; Gong, H. Chem. Asian J. 2017, 12, 2524. |
| [67] | Majumdar, B.; Sarma, D.; Bhattacharya, T.; Sarma, T. K. ACS Sustainable Chem. Eng. 2017, 5, 9286. |
| [68] | Shaikh, M.; Sahu, A.; Kiran Kumar, A.; Sahu, M.; Singh, S. K.; Ranganath, K. V. S. Green Chem. 2017, 19, 4533. |
| [69] | Fang, J.; Peng, Z.; Yang, Y.; Wang, J.; Guo, J.; Gong, H. Asian J. Org. Chem. 2018, 7, 355. |
| [70] | Su, C.; Acik, M.; Takai, K.; Lu, J.; Hao, S.-j.; Zheng, Y.; Wu, P.; Bao, Q.; Enoki, T.; Chabal, Y. J.; Ping Loh, K. Nat. Commun. 2012, 3, 1298. |
/
| 〈 |
|
〉 |
