三苯胺功能化有序介孔聚合物作为无金属光催化剂用于二硫化物合成
收稿日期: 2023-08-07
修回日期: 2023-09-27
网络出版日期: 2023-10-26
基金资助
国家自然科学基金(22071092); 甘肃省科技重大专项(22ZD6FA006); 甘肃省自然科学基金(23JRRA1044)
Triphenylamine-Based Ordered Mesoporous Polymer as a Metal-Free Photocatalyst for Oxidation of Thiols to Disulfide
Received date: 2023-08-07
Revised date: 2023-09-27
Online published: 2023-10-26
Supported by
National Natural Science Foundation of China(22071092); Science and Technology Major Program of Gansu Province(22ZD6FA006); Natural Science Foundation of Gansu Province(23JRRA1044)
有机二硫化物广泛存在于活性天然产物及药物分子中, 其在生物领域也有广泛的用途. 可见光促进的两分子硫醇间的氧化偶联是制备对称二硫化物绿色、高效和原子经济的方法之一, 但是此类反应所使用的光敏剂(金属配合物、有机小分子及无机半导体等)分别具有价格昂贵、光稳定性差、可见光吸收范围窄及易于被光腐蚀等问题. 因此, 开发价格便宜、稳定性好以及可回收的非金属光催化体系, 降低大规模合成的成本依然是该领域亟需解决的问题. 在此, 报道了一种三苯胺功能化的有序介孔聚合物(TPA-MPs)作为非金属多相光催化剂催化的硫醇/硫酚需氧氧化偶联反应. 该反应可在室温和空气氛围下高效合成多种二硫化物. TPA-MPs催化剂可重复使用6次以上而光催化活性无明显下降. 开发的多相光催化体系具有操作简便、反应条件温和和绿色环保等优点, 并且可以有效放大至克级规模, 为有机二硫化物的合成提供了新颖高效的工具.
刘继宇 , 李圣玉 , 陈款 , 朱茵 , 张元 . 三苯胺功能化有序介孔聚合物作为无金属光催化剂用于二硫化物合成[J]. 有机化学, 2024 , 44(2) : 605 -612 . DOI: 10.6023/cjoc202308006
Disulfides are widely present in biologically active natural products and pharmaceuticals, and they also have a wide range of applications in life sciences. The visible light-induced oxidative coupling of two thiols is one of the most efficient, atomically economical and green method for the preparation of symmetric disulfides. However, the photocatalysts used in these reactions (metal complexes, small organic molecules and inorganic semiconductors, etc.) are facing problems such as expensive, poor photostability, limited visible-light absorption and photocorrosion. Thus, it is still highly desirable to develop efficient heterogeneous photocatalysts that are free of precious metals, inexpensive, stable and recyclable, to decrease the processing costs in large-scale synthesis. Herein, a triphenylamine-based ordered mesoporous polymers (TPA-MPs) as a metal-free photocatalyst for oxidation of thiols to disulfide was reported. This protocol provides a facile means for the rapid synthesis of a series of disulfides at room temperature under air atmosphere. TPA-MPs can be easily recovered with good retention of photocatalytic activity and reused at least six times. This approach is operationally simple, mild, green, and scalable, providing a facile and efficient access to disulfides.
| [1] | (a) Liu, T.; Wang, Y.; Luo, X.; Li, J.; Reed, S. A.; Xiao, H.; Young, T. S.; Schultz, P. G. Proc. Natl. Acad. Sci. U. S. A. 2016, 113, 5910. |
| [1] | (b) Sevier, C. S.; Kaiser, C. A. Nat. Rev. Mol. Cell Biol. 2002, 3, 836. |
| [1] | (c) Wommack, A. J.; Ziarek, J. J.; Tomaras, J.; Chileveru, H. R.; Zhang, Y.; Wagner, G.; Nolan, E. M. J. Am. Chem. Soc. 2014, 136, 13494. |
| [2] | Jiang, C.-S.; Mu?ller, W. E. G.; Schro?der, H. C.; Guo, Y.-W. Chem. Rev. 2012, 112, 2179. |
| [3] | (a) Li, B.; Wever, W. J.; Walsh, C. T.; Bowers, A. A. Nat. Prod. Rep. 2014, 31, 905. |
| [3] | (b) Chan, A. N.; Shiver, L. S.; Wever, W. J.; Razvi, S. Z. A.; Traxler, M. F.; Li, B. Proc. Natl. Acad. Sci. U. S. A. 2017, 114, 2717. |
| [4] | Witt D. Synthesi. 2008, 16, 2491. |
| [5] | Li, X.-B.; Li, Z.-J.; Gao, Y.-J.; Meng, Q.-Y.; Yu, S.; Weiss, R. G.; Tung, C.-H.; Wu, L.-Z. Angew. Chem.. Int. Ed. 2014, 53, 2085. |
| [6] | Scharf, D. H.; Groll, M.; Habel, A.; Heinekamp, T.; Hertweck, C.; Brakhage, A. A.; Huber, E. M. Angew. Chem.. Int. Ed. 2014, 53, 2221. |
| [7] | Garrett, C. E.; Prasad, K. Adv. Synth. Catal. 2004, 346, 889. |
| [8] | (a) Liu, Q.; Wu, L.-Z. Natl. Sci. Rev. 2017, 4, 35. |
| [8] | (b) Dai, X. J.; Xu, X. L.; Li, X. N. Chin. J. Org. Chem. 2013, 33, 2046 (in Chinese). |
| [8] | (戴小军, 许孝良, 李小年, 有机化学. 2013, 33, 2046.) |
| [9] | Dethe, D. H.; Srivastava, A.; Dherange, B. D.; Kumar, B. V. Adv. Synth. Catal. 2018, 360, 3020. |
| [10] | (a) Talla, A.; Driessen, B.; Straathof, N. J. W.; Milroy, L.-G.; Brunsveld, L.; Hessel, V.; No?l, T. Adv. Synth. Catal. 2015, 357, 2180. |
| [10] | (b) Spiliopoulou, N.; Kokotos, C. G. Green Chem. 2021, 23, 546. |
| [11] | (a) Bottecchia, C.; Erdmann, N.; Tijssen, P. M. A.; Milroy, L.-G.; Brunsveld, L.; Hessel, V.; No?l, T. ChemSusChe. 2016, 9, 1781. |
| [11] | (b) Xu, H.; Shi, J.-L.; Lyu, S.; Lang, X. Chin. J. Catal. 2020, 41, 1468. |
| [12] | Wu, W.-B.; Wong, Y.-C.; Tan, Z.-K.; Wu, J. Catal. Sci. Technol. 2018, 8, 4257. |
| [13] | Sha, Y.; Lin, X.-M.; Niklas, J.; Poluektov, O. G.; Diroll, B. T.; Lin, Y.; Wen, J.; Hood, Z. D.; Lei, A.; Shevchenko, E. V. J. Mater. Chem. . 2021, 9, 12690. |
| [14] | Savateev, A.; Ghosh, I.; K?nig, B.; Antonietti, M. Angew. Chem.. Int. Ed. 2018, 57, 15936. |
| [15] | Quan, Y.; Lan, G.; Fan, Y.; Shi, W.; You, E.; Lin, W. J. Am. Chem. Soc. 2020, 142, 1746. |
| [16] | Wang W. Acta Chim. Sinic. 2015, 73, 461 (in Chinese). |
| [16] | (王为, 化学学报 2015, 73, 461.) |
| [17] | Xu, Z. Y.; Luo, Y.; Wang, H.; Zhang, D. W.; Li, Z. T. Chin. J. Org. Chem. 2020, 40, 3777 (in Chinese). |
| [17] | (徐子悦, 罗驿, 王辉, 张丹维, 黎占亭, 有机化学. 2020, 40, 3777.) |
| [18] | Meng, Y.; Gu, D.; Zhang, F.; Shi, Y.; Yang, H.; Li, Z.; Yu, C.; Tu, B.; Zhao, D. Angew. Chem.. Int. Ed. 2005, 44, 7053. |
| [19] | Wang, X.; Chen, L.; Chong, S. Y.; Little, M. A.; Wu, Y.; Zhu, W.-H.; Clowes, R.; Yan, Y.; Zwijnenburg, M. A.; Sprick, R. S.; Cooper, A. I. Nat. Chem. 2018, 10, 1180. |
| [20] | (a) Xing, R.; Liu, N.; Liu, Y.; Wu, H.; Jiang, Y.; Chen, L.; He, M.; Wu, P. Adv. Funct. Mater. 2007, 17, 2455. |
| [20] | (b) Liu, F.; Zuo, S.; Kong, W.; Qi, C. Green Chem. 2012, 14, 1342. |
| [20] | (c) Zhang, F.; Yang, X.; Jiang, L.; Liang, C.; Zhu, R.; Li, H. Green Chem. 2013, 15, 1665. |
| [21] | (a) Zhang, F.; Liang, C.; Wu, X.; Li, H. Angew. Chem.. Int. Ed. 2014, 53, 8498. |
| [21] | (b) Zhang, F.; Yang, X.; Zhu, F.; Huang, J.; He, W.; Wang, W.; Li, H. Chem. Sci. 2012, 3, 476. |
| [22] | Zhang, W.; Mei, Y.; Huang, X.; Wu, P.; Wu, H.; He, M. ACS Appl. Mater. Interface. 2019, 11, 44241. |
| [23] | Liu, F.; Wu, Q.; Liu, C.; Qi, C.; Huang, K.; Zheng, A.; Dai, S. ChemSusChe. 2016, 9, 2496. |
| [24] | (a) Yang, X.; Li, L.; Li, Y.; Zhang, Y. J. Org. Chem. 2016, 81, 12433. |
| [24] | (b) Li, S.; Yang, X.; Wang, Y.; Zhou, H.; Zhang, B.; Huang, G.; Zhang, Y.; Li, Y. Adv. Synth. Catal. 2018, 360, 4452. |
| [24] | (c) Zhang, Y.; Yang, X.; Zhou, H.; Li, S.; Zhu, Y.; Li, Y. Org. Chem. Front. 2018, 5, 2120. |
| [24] | (d) Zhou, H.; Yang, X.; Li, S.; Zhu, Y.; Li, Y.; Zhang, Y. Org. Biomol. Chem. 2018, 16, 6728. |
| [24] | (e) Wang, J.; Li, L.; Guo, Y.; Li, S.; Wang, S.; Li, Y.; Zhang, Y. Org. Biomol. Chem. 2020, 18, 8179. |
| [24] | (f) Zhang, Y.; Li, S.; Zhu, Y.; Yang, X.; Zhou, H.; Li, Y. J. Org. Chem. 2020, 85, 6261. |
| [24] | (g) Yang, X.; Zhu, Y.; Xie, Z.; Li, Y.; Zhang, Y. Org. Lett. 2020, 22, 1638. |
| [24] | (h) Yang, X.; Xie, Z.; Li, Y.; Zhang, Y. Chem. Sci. 2020, 11, 4741. |
| [24] | (i) Wang, S.; Ye, Y.; Hu, Y.; Meng, X.; Liu, Z.; Liu, J.; Chen, K.; Zhang, Z.; Zhang, Y. Chem. Commun. 2023, 59, 2628. |
| [25] | (a) Lan, Y.; Yang, C.; Zhang, Y.; An, W.; Xue, H.; Ding, S.; Zhou, P.; Wang, W. Polym. Chem. 2019, 10, 3298. |
| [25] | (b) Guo, Y.; Wang, W. D.; Li, S.; Zhu, Y.; Wang, X.; Liu, X.; Zhang, Y. Chem Asian J. 2021, 16, 3689. |
| [26] | Zhu, Y.; Li, S.; Yang, X.; Wang, S.; Zhang, Y. J. Mater. Chem. . 2022, 10, 13978. |
| [27] | Li, X.; Fan, J.; Cui, D.; Yan, H.; Shan, S.; Lu, Y.; Cheng, X.; Loh, T.-P. Eur. J. Org. Chem. 2022, e202200340. |
| [28] | Wang, G.; Jia, J.; He, Y.; Wei, D.; Song, M.; Zhang, L.; Li, G.; Li, H.; Yuan, B. RSC Adv. 2022, 12, 18407. |
| [29] | Bettanin, L.; Saba, S.; Galetto, F. Z.; Mike, G. A.; Rafique, J.; Braga, A. L. Tetrahedron Lett. 2017, 58, 4713. |
| [30] | Huo, S.; Shi, H.; Liu, D.; Shen, S.; Zhang, J.; Song, C.; Shi, T. J. Inorg. Biochem. 2013, 125, 9. |
| [31] | Bartoccini, F.; Retini, M.; Crinelli, R.; Menotta, M.; Fraternale, A.; Piersanti, G. J. Org. Chem. 2022, 87, 10073. |
| [32] | Nguyen, N.-G. T.; Nguyen, X.-T.; Nguyen, N.-H.; Luu, T. X. T.; Dao, X.-T. J. Sulfur Chem. 2022, 43, 593. |
| [33] | Song, M.; Hu, Q.; Li, Z.-Y.; Sun, X.; Yang, K. Chin. Chem. Lett. 2022, 33, 4269. |
| [34] | Ren, M.-Z.; Fu, Y.-J.; Zhang, B.-S.; Quan, Z.-J.; Wang, X.-C. Synthesi. 2023, 55, 2011. |
| [35] | Ma, Y.-T.; Lin, C.; Huang, X.-B.; Liu, M.-C.; Zhou, Y.-B.; Wu, H.-Y. Chem. Commun. 2022, 58, 6550. |
/
| 〈 |
|
〉 |
