N-溴代丁二酰亚胺促进的P(O)-H化合物参与的醇的直接磷酸化反应
收稿日期: 2024-04-15
修回日期: 2024-05-08
网络出版日期: 2024-05-23
基金资助
贵州省中医药管理局课题(QZYY-2021-008); 国家自然科学基金(82360679); 贵州省基础研究(自然科学方向)(黔科合基础-ZK[2022]一般592)
N-Bromosuccinimide-Promoted Direct Phosphorylation of Alcohols with P(O)-H Compounds
Received date: 2024-04-15
Revised date: 2024-05-08
Online published: 2024-05-23
Supported by
Guizhou Provincial Administration of Traditional Chinese Medicine Project(QZYY-2021-008); National Natural Science Foundation of China(82360679); Guizhou Provincial Basic Research Program (Natural Science)(QKHJC-ZK[2022] General 592)
发展了一种温和、绿色、便捷和可扩大的N-溴代丁二酰亚胺(NBS)促进的次级膦氧化合物与醇的直接磷酸化策略, 用于合成多种次磷酸酯. 底物适用范围广泛且耐受性好, 能以中等至优异的收率(高达92%)合成目标化合物. 该反应在室温下进行, 无需添加任何氧化剂和金属催化剂, 为次磷酸酯衍生物的合成提供了一种新的策略.
关键词: 磷酸化; P—O键; 次磷酸酯; 醇; N-溴代丁二酰亚胺(NBS)
王华斌 , 徐连华 , 刘雄伟 , 潘博文 , 姚震 , 黄强 , 周英 . N-溴代丁二酰亚胺促进的P(O)-H化合物参与的醇的直接磷酸化反应[J]. 有机化学, 2024 , 44(9) : 2847 -2853 . DOI: 10.6023/cjoc20203002
A mild, green, convenient and scalable N-bromosuccinimide (NBS) promoted direct phosphorylation strategy of secondary phosphine oxides and alcohols for the synthesis of various phosphinate esters was developed. A variety of substrates are well-tolerated and the desirable compounds were afforded in moderate to excellent yields (up to 92%). This reaction is conducted at room temperature without the addition of any oxidant and metal catalyst, which provides a new strategy for the synthesis of phosphinate esters.
Key words: phosphorylation; P—O bond; phosphinate ester; alcohol; N-bromosuccinimide (NBS)
| [1] | (a) Rodriguez, J. B.; GalloRodriguez, C. Chem. Med. Chem. 2019, 14, 190. |
| [1] | (b) Derstine, B. P.; Tomlin, J. W.; Peck, C. L.; Dietz, J. P.; Herrera, B. T.; Cardoso, F. S. P.; Paymode, D. J.; Yue, A. C.; Arduengo III, A. J.; Opatz, T.; Snead, D. R.; Stringham, R. W.; McQuade, D. T.; Gupton, B. F. Org. Process. Res. Dev. 2020, 24, 1420. |
| [1] | (c) Wojtczak, B. A.; Sikorski, P. J.; Fac Dabrowska, K.; Nowicka, A.; Warminski, M.; Kubacka, D.; Nowak, E.; Nowotny, M.; Kowalska, J.; Jemielity, J. J. Am. Chem. Soc. 2018, 140, 5987. |
| [1] | (d) Knouse, K. W.; Justine, N.; Schmidt, M. A.; Zheng, B.; Vantourout, J. C.; Kingston, C.; Mercer, S. E.; Mcdonald, I. M.; Olson, R. E.; Zhu, Y. Science 2018, 361, 1234. |
| [1] | (e) Wang, J.; Liu, L.-Y.; Xu, W.-B.; Yang, Z.-C.; Yan, Y.-C.; Xie, X.-X.; Wang, Y.; Yi, T.; Wang, C.-Y.; Hua, J.-L. Anal. Chem. 2019, 91, 5786. |
| [1] | (f) Huang, H.; Denne, J.; Yang, C.-H.; Wang, H.; Kang, J.-Y. Angew. Chem., Int. Ed. 2018, 57, 6624. |
| [2] | (a) Ou, Y.-C.; Huang, Y.-T.; He, Z.-L.; Yu, G.-D.; Huo, Y.-P.; Li, X.-W.; Gao, Y.; Chen, Q. Chem. Commun. 2020, 56, 1357. |
| [2] | (b) Wang, W.-Y.; Jin, H.-G.; Yan, Z.-H.; He, M.-C.; Lin, S.; Tian, W.-S. Tetrahedron Lett. 2017, 58, 3489. |
| [3] | (a) Atherton, F. R.; Todd, A. R. J. Chem. Soc. 1947, 674. |
| [3] | (b) Xiong, B.-Q.; Zhou, Y.-B.; Zhao, C.-Q.; Goto, M.; Yin, S.-F.; Han, L.-B. Tetrahedron 2013, 69, 9373. |
| [3] | (c) Ashmus, R. A.; Lowary, T. L. Org. Lett. 2014, 16, 2518. |
| [3] | (d) Fang, S. Q.; Liu, Z. J.; Wang, T. L. Chin. J. Org. Chem. 2023, 43, 1069 (in Chinese). |
| [3] | (方思强, 刘赞娇, 王天利, 有机化学, 2023, 43, 1069.) |
| [4] | Hua, Y.-X.; Lin, Y.-C.; Chen, W.-Y.; Ye, L.-Y.; Yin, Y.-W.; Gao, Y.-X.; Tu, S. Tetrahedron Lett. 2022, 99, 153822. |
| [5] | Shen, J.; Li, Q.-W.; Zhang, X.-Y.; Wang, X.; Li, G.-Z.; Li, W.-Z.; Yang, S.-D.; Yang, B. Org. Lett. 2021, 23, 1541. |
| [6] | Li, C.-Y.; Chen, T.-Q.; Han, L.-B. Dalton Trans. 2016, 45, 14893. |
| [7] | Dhineshkumar, J.; Prabhu, K. R. Org. Lett. 2013, 15, 6062. |
| [8] | Li, Y.-J.; Yang, Q.; Yang, L.-Q.; Zheng, K. Chem. Commun. 2019, 55, 4981. |
| [9] | (a) Zhong, W.-W.; Zhang, Q.; Li, M.-S.; Hu, D.-Y.; Cheng, M.; Du, F.-T.; Ji, J.-X.; Wei, W. Synth. Commun. 2016, 46, 1377. |
| [9] | (b) Zhang, Z.-J.; Yi, D.; Fu, Q.; Liang, W.; Chen, S.-Y.; Yang, L.; Du, F.-T.; Ji, J.-X.; Wei, W. Tetrahedron Lett. 2017, 58, 2417. |
| [9] | (c) Liang, W.; Zhang, Z.-J.; Yi, D.; Fu, Q.; Chen, S.-Y.; Yang, L.; Du, F.-T.; Ji, J.-X.; Wei, W. Chin. J. Chem. 2017, 35, 1378. |
| [9] | (d) Yi, D.; Fu, Q.; Chen, S.-Y.; Gao, M.; Zhang, Z.-J.; Liang, W.; Zhang, Q.; Ji, J.-X.; Wei, W. ; Tetrahedron Lett. 2017, 58, 2058. |
| [10] | (a) Chen, D.-F.; Chrisman, C. H.; Miyake, G. M. ACS Catal. 2020, 10, 2609. |
| [10] | (b) Zidan, M.; McCallum, T.; Swann, R.; Barriault, L. Org. Lett. 2020, 22, 8401. |
| [10] | (c) Wang, H.; Liu, H.-W.; Wang, M.; Huang, M.-R.; Shi, X.-C.; Wang, T.-L.; Cong, X.; Yan, J.-M.; Wu, J. Science 2021, 24, 102693. |
| [10] | (d) Gembreska, N. R.; Vogel, A. K.; Ziegelmeyer, E. C.; Cheng, E.; Wu, F.; Roberts, L. P.; Vesoulis, M. M.; Li, W. Synlett 2021, 32, 539. |
| [10] | (e) Wang, H.-K.; Ren, X.-L.; Xuan, Y.-N. Chin. J. Org. Chem. 2024, 44, 251 (in Chinese). |
| [10] | (王化坤, 任晓龙, 宣宜宁, 有机化学, 2024, 44, 251.) |
| [10] | (f) Qian, C.-W.; Han, R.; Shen, Z.-X.; Li, Q.; Chen, X.-R. Chin. J. Org. Chem. 2022, 42, 2496 (in Chinese). |
| [10] | (钱存卫, 韩容, 沈芷欣, 李倩, 陈选荣, 有机化学, 2022, 42, 2496.) |
| [11] | Li, Y.-J.; Liang, F.-S. Tetrahedron Lett. 2016, 57, 2931. |
| [12] | (a) Li, Q.-Y.; Swaroop, T. R.; Hou, C.; Wang, Z.-Q.; Pan, Y.-M.; Tang, H.-T. Adv. Synth. Catal. 2019, 361, 1761. |
| [12] | (b) Yu, X.-J.; Zhang, S.; Jiang, Z.-Y.; Zhang, H.-S.; Wang, T.-L. Eur. J. Org. Chem. 2020, 20, 3110. |
| [12] | (c) Deng, L.-L.; Wang, Y.; Mei, H.-B.; Pan, Y.; Han, J.-L. J. Org. Chem. 2019, 84, 949. |
| [12] | (d) Tan, Y.-S.; Han, Y.-P.; Zhang, Y.-C.; Zhang, H.-Y.; Zhao, J.-Q.; Yang, S.-D. J. Org. Chem. 2022, 87, 3254. |
| [12] | (e) Li, C.-J. Chin. J. Chem. 2022, 40, 838. |
| [13] | (a) Huang, Y.-Y.; Wang, N.; Wu, Z.-G.; Wu, X.-X.; Wang, M.-K.; Huang, W.-C.; Zi, Y. Org. Lett. 2023, 25, 7595. |
| [13] | (b) Zhang, J.-S.; Zhang, J.-Q.; Chen, T.-Q.; Han, L.-B. Org. Biomol. Chem. 2017, 15, 5462. |
| [13] | (c) Gao, Y.-Z.; Tang, G.; Zhao, Y.-F. Chin. J. Org. Chem. 2018, 38, 62 (in Chinese). |
| [13] | (高玉珍, 唐果, 赵玉芬, 有机化学, 2018, 38, 62.) |
| [13] | (d) Yang, J.; Xiao, J.; Zhou, Y.-B.; Chen, T.-Q.; Yin, S.-F.; Han, L.-B. Chin. J. Org. Chem. 2017, 37, 1055 (in Chinese). |
| [13] | (杨佳, 肖晶, 周永波, 陈铁桥, 尹双凤, 韩立彪, 有机化学, 2017, 37, 1055.) |
| [13] | (e) Yang, B.; Tian, Q.-P.; Yang, S.-D. Chin. J. Org. Chem. 2014, 34, 717 (in Chinese). |
| [13] | (杨斌, 田秋萍, 杨尚东, 有机化学, 2014, 343, 717.) |
/
| 〈 |
|
〉 |