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0 7035

DOI: https://doi.org/10.6023/cjoc202507035

研究论文

N-溴代丁二酰亚胺促进的P(O)-H化合物参与的胺的直接磷酰化反应

  • 李乔莉 ,
  • 王华斌 ,
  • 覃燕 ,
  • 赵加敏 ,
  • 韩芳 ,
  • 刘雄伟 ,
  • 潘博文 ,
  • 黄强 ,
  • 周英
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  • a贵州中医药大学 药学院 贵阳 550025;
    b遵义医科大学 药学院 遵义 563000;
    c贵州省现代中药创制全省重点实验室 贵阳 550025
†共同第一作者

收稿日期: 2025-10-08

  修回日期: 2025-11-01

  网络出版日期: 2025-11-27

基金资助

贵州省自然科学基金课题(黔科合基础-ZK[2024]青年046,黔科合基础-ZK[2025]面上170）资助项目、贵州省现代中药创新重点实验室; （黔科合平台 ZSYS [2025] 019）和贵州省高层次创新人才（黔科合平台人才-GCC [2023] 047）的资助项目

收起

N-Bromosuccinimide-Promoted Direct Phosphorylation of Amines with P(O)-H Compounds

  • Li Qiaoli ,
  • Wang Huabin ,
  • Qin Yan ,
  • Zhao Jiamin ,
  • Han Fang ,
  • Liu Xiongwei ,
  • Pan Bowen ,
  • Huang Qiang ,
  • Zhou Ying
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  • aGuizhou University of Traditional Chinese Medicine, College of pharmacy, Guiyang 550025, China;
    bZunyi Medical University, School of Pharmacy, Zunyi 563000, China;
    cGuizhou Key Laboratory of Modern Traditional Chinese Medicine Creation, Guiyang 550025, China
†These authors contributed equally to this work.

Received date: 2025-10-08

  Revised date: 2025-11-01

  Online published: 2025-11-27

Supported by

Guizhou Provincial Natural Science Foundation (QKHJC-ZK[2024]Qiannian046,QKHJC-ZK [2025] mianshang 170), Guizhou Key Laboratory of Modern Traditional Chinese Medicine Creation (Qian Ke He Platform ZSYS [2025] 019) andHigh-level Innovative Talents of Guizhou Province (QianKeHe platform talents-GCC [2023] 047).

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摘要

发展了一种温和、绿色、高原子经济性、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胺的直接磷酰化策略用于合成多种磷酰胺类化合物。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93%）合成目标化合物。该反应在空气中和室温下进行,无需添加金属催化剂、碱和高的反应温度,这为磷酰胺衍生物的合成提供了一种新的策略。

关键词： 磷酰化; P(O)-N键; 磷酰胺类化合物; 胺; N-溴代丁二酰亚胺

本文引用格式

李乔莉 , 王华斌 , 覃燕 , 赵加敏 , 韩芳 , 刘雄伟 , 潘博文 , 黄强 , 周英 . N-溴代丁二酰亚胺促进的P(O)-H化合物参与的胺的直接磷酰化反应[J]. 有机化学, 0 : 7035 . DOI: 10.6023/cjoc202507035

Abstract

A mild, green, high atom economic, convenient and scalable N-Bromosuccinimide (NBS) promoted direct phosphorylation strategy of secondary phosphine oxides and amines for the synthesis of various valuable phosphamide compounds was developed. A variety of substrates were well-tolerated and afforded the desirable compounds in moderate to excellent yields (up to 93%). This reaction was conducted at room temperature under air without additive of metal catalyst, base or high temperature, providing a new strategy for the synthesis of phosphamide compounds.

Key words： Phosphorylation; P(O)-N bond; Phosphamide compounds; Amines; N-Bromosuccinimide

参考文献

[1] (a) Wang, Y.-Q.; Soldatov, M.; Wang, Q.-Z.; Liu, H.-Z.Polymer., 2021, 218, 123491-123499.
(b) Jakob, W.; Mohamed, A.; David, B. Eur. J. Org. Chem., 2019, 2019, 442-450.
(c) Kozma, V.; Fülöp, F.; Szőllősi, G. Adv. Synth. Catal., 2020, 362, 2444-2458.
[2] (a) Gholivand, K.; Dashtaki, M. R.; Ardebili, S. A. A.; Mohammadpour, M.; Valmoozi, A. A. E.J. Mol. Struct., 2021, 1240, 130528.
(b) Zhu, Y.-Y.; Niu, Y.; Niu, Y.-N.; Yang, S.-D. Org. Biomol. Chem., 2021, 19, 10296-10313.
(c) Lin, Z.-Q.; Pang, S.-M.; Zhang, W.-P.; Mishra, S.; Bhatt, P.; Chen, S.-H. Front. Microbiol., 2020, 11, 2045-2051.
(d) Logeshwaran, P.; Krishnan, K.; Naidu, R.; Megharaj, M. Chemosphere, 2020, 252, 126549-126553.
(e) Jegan, G.; Mishra, S.; Sreenivasulu, B.; Rajesh, P.; Suresh, A.; Rao, C. V. S. B.; Sivaraman, N. Results Chem., 2022, 4, 100346.
(f) Jiang, Z.-M.; Li, H.-Y.; Zhang, C.-X.; Zhu, P. Surf. Interfaces., 2022, 34,102409.
(g) Boggiano, A. C.; Bernbeck, M. G.; Jiang N.-X.; Pierre, H. S. L. Inorg. Chem., 2024, 63, 9638-9647.
(h) Sachin, A. R.; Gopakumar, G.; Rao, C. V. S. B. Results Chem., 2024, 7, 101498.
(i) Ma, Y.-N.; Zhang, X.; Yang, S.-D. Chem. Eur. J., 2017, 23, 3007-3011.
(j) Ma, Y.-N.; Chen, M.-X.; Yang, S.-D. Org. Lett., 2017, 19, 600-603.
[3] (a) Singh, K.; Trappanese, D. M.; Moreland, R. S.Eur. J. Med. Chem., 2012, 54, 397-402.
(b) Xu, W.; Li, W.; Ren, M.; Yin, J. Asian J. Chem., 2013, 25, 5683-5685.
[4] (a) Atherton, F. R.; Todd, A. R.J.Chem. Soc., 1947, 674-678.
(b) Xiong, B.-Q.; Zhou, Y.-B.; Zhao, C.-Q.; Goto, M.; Yin, S.-F.; Han, L.-B. Tetrahedron., 2013, 69, 9373.
(c) Ashmus, R. A.; Lowary, T. L. Org. Lett., 2014, 16, 2518.
(d) Fang, S. Q.; Liu, Z.-J.; Wang, T.-L. Chin. J. Org. Chem., 2023, 43, 1069-1083 (in Chinese).
(方思强, 刘赞娇, 王天利, 有机化学, 2023, 43, 1069-1083.)
(e) 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, 1357-1360.
(f) Ding, T.-T.; Qin, C.-C.; Gao, D.-D.; Li, X.-J.; Yan, H.; Liu, R.-M.; Zhao, C.-Q.; Nie, S.-Z. Phosphorus Sulfur Relat. Elem., 2019, 194, 102-110.
[5] Kaboudin B.;Donyavi A.; Kazemi, F.Synthesis., 2018, 50, 170-174.
[6] 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, 1357-1361.
[7] Tan C.; Liu X.; Jia H.; Zhao X.; Chen J.; Wang Z.; Tan, J.Chem.-Eur. J., 2019, 26, 881-887.
[8] Wang Z.-Z.; Huang L.-H.; Huang R.; Wang J.; Cheng, C.-R.Org. Biomol. Chem., 2025, 23, 1320-1324.
[9] Meazza M.; Kowalczuk A.; Shirley L.; Yang J.-W.; Guo H.; Rios, R.Adv. Synth. Catal., 2016, 358, 719-723.
[10] Deng Y.; You S.; Ruan M.; Wang Y.; Chen Z.; Yang G.; Gao, M.Adv. Synth. Catal., 2020, 363, 464-469.
[11] Abraham T. W.; Kalman T. I.; McIntee E. J.; Wagner, C. R.J. Med. Chem., 1996, 39, 4569-4575.
[12] (a) Zheng, H.; Liu, C.-H.; Guo, S.-Y.; He, G.-C.; Min, X.-T.; Zhou, B.-C.; Ji, D.-W.; Hu Y.-C.; Chen, Q.-A.Nat Commun., 2022, 13, 3496.
(b) Vil’, V. A.; Krylov, I. B.; Terent’ev, A. O. Sci. China Chem., 2021, 64, 681-683.
(c) Li, H.; Yu, K.-C.; Su, J.-K.; Yang, W.-O.; Fan N.-L.; Hu, X.-G. Green Chem., 2022, 24, 8280-8291.
(d) Ci, R.-N.; Huang, C.; Zhao, L.-M.; Qiao, J.; Chen, B.; Feng, K.; Tung C.-H.; Wu, L.-Z. CCS Chem., 2022, 4, 2946-2952.
(e) Duan, D.-H.; He, H.-P.; Ding, W.-Y.; Yi, D.-C.; Lai, Y.-Z.; Huang, A.-Q.; Liu, J.; Wu W.-L.; Peng, X.-J. Org. Chem. Front., 2023, 10, 6055-6062.
(f) Liang, S.-Y.; Hemberger, P.; Steglich, M.; Simonetti, P.; Levalois-Grützmacher, J.; Grützmacher H.; Gaan, S. CHEM-EUR J., 2020, 26, 10795-10800.
(g) Zhang, Z.; Liu, M.-R.; Liu, M.; Pan, C.-H.; Mao Z.-T.; Zhang, X.-X. J. Org. Chem., 2024, 89, 2996-3009.
[13] (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, 1377-1385.
(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, 2417-2420.
(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, 1378-138.
(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, 2058-2061.
(e) Wang, H.-B.; Xu, L.-H.; Liu, X.-W.; Shi, Y.; Yao, Z.; Zhou, Y.; Huang, Q. Org. Biomol. Chem., 2024, 22, 7518-7523.
(f) Wang, H.-B.; Xu, L.-H.; Liu, X.-W.; Pan, B.-W.; Yao, Z.; Huang, Q.; Zhou, Y. Chin. J. Org. Chem., 2024, 44, 847-2853.
[14] (a) Chen, D.-F.; Chrisman, C. H.; Miyake, G. M.ACS Catalysis., 2020, 10, 2609-2614.
(b) Zidan, M.; McCallum, T.; Swann, R.; Barriault, L. Org. Lett., 2020, 22, 8401-8406
(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.
(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, 539-544.
(e) Wang, H.-K.; Ren, X.-L,; Xuan,Y.-N. Chin. J. Org. Chem., 2024, 44, 251-258 (in Chinese).
(王化坤, 任晓龙, 宣宜宁, 有机化学, 2024, 44, 251-258.)
(f) Qian, C.-W.; Han, R.; Shen, Z.-X.; Li, Q.; Chen, X.-R. Chin. J. Org. Chem., 2022, 42, 2496-2503 (in Chinese).
(钱存卫, 韩容, 沈芷欣, 李倩, 陈选荣, 有机化学, 2022, 42, 2496-2503.)
[15] Li Y.-J.; Liang F.-S.Tetrahedron Lett., 2016, 57, 2931-2934.
[16] (a) Huang, Y.-Y.; Wang, N.; Wu, Z.-G.; Wu, X.-X.; Wang, M.-K.; Huang, W.-C.; Zi, Y. Org. Lett., 2023, 25, 7595-7600.
(b) Zhang, J.-S.; Zhang, J.-Q.; Chen, T.-Q.; Han, L.-B. Org. Biomol. Chem., 2017, 15, 5462-5467.
(c) Gao, Y.-Z.; Tang, G.; Zhao, Y.-F. Chin. J. Org. Chem., 2018, 38, 62-74 (in Chinese).
(高玉珍, 唐果, 赵玉芬, 有机化学, 2018, 38, 62-74.)
(d) Yang, J.; Xiao, J.; Zhou, Y.-B.; Chen, T.-Q.; Yin, S.-F.; Han, L.-B. Chin. J. Org. Chem., 2017, 37, 1055-1068 (in Chinese).
(杨佳, 肖晶, 周永波, 陈铁桥, 尹双凤, 韩立彪, 有机化学, 2017, 37, 1055-1068.)
(e) Yang, B.; Tian, Q.-P.; Yang, S.-D. Chin. J. Org. Chem., 2014, 34, 717-721 (in Chinese).
(杨斌, 田秋萍, 杨尚东, 有机化学, 2014, 343, 717-721.)
[17] (a) Huang, Q.; Dong, K.-K.; Bai, W.-J.; Yi, D.; Ji J.-X.; Wei, W.Org. Lett., 2019, 21, 3332-3336.
(b) Wang, H.-B.; Fu, Q.; Zhang, Z.-J.; Gao, M.; Ji J.-X.; Yi, D. Chin. J. Org. Chem., 2018, 38, 1977-1984.
[18] (a) Ma, C.-H.; Li, X.-F.; Chen, X.-Y.; He, X.; Zhang, S.-T.; Jiang Y.-Q. ; Yu, B.Org. Lett., 2023, 25, 8016-8021.
(b) Zeng, J.-H.; Du, D.-T.; Liu, B.-E.; Zhang Z.-Q.; Zhan, Z.-P. J. Org. Chem., 2023, 88, 14789-14796.
(c) Zhang, G.-X.; He, H.; Chen, X.-X.; Ni S.-F.; Zeng, R. Org. Lett., 2023, 25, 5356-5360.
(d) Zhang, Y.; Guo, Y.-C.; Zhao Y.-F.; Cao, S.-X. J. Org. Chem., 2024, 89, 3259-3270.
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