NBS-Promoted Direct Phosphorylation of Alcohols with P(O)-H Compounds

doi:10.6023/cjoc202403002

Chinese Journal of Organic Chemistry Next Articles

NBS促进的P(O)-H化合物参与的醇的直接磷酸化反应

王华斌^†,a, 徐连华^†,a, 刘雄伟^a, 潘博文^a, 姚震^a, 黄强^*,b, 周英^*,a

^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

收稿日期:2024-04-15 修回日期:2024-05-08
作者简介:^†共同第一作者
基金资助:
贵州省中医药管理局课题(No.QZYY-2021-008)资助项目, 国家自然科学基金(No.82360679)资助项目, 贵州省基础研究项目(自然科学方向)(黔科合基础-ZK[2022]一般592)资助项目.

NBS-Promoted Direct Phosphorylation of Alcohols with P(O)-H Compounds

Wang, Huabin^†,a, Xu, Lianhua^†,a, Liu, Xiongwei^a, Pan, Bowen^a, Yao, Zhen^a, Huang, Qiang^*,b, Zhou, Ying^*,a

^aGuizhou University of Traditional Chinese Medicine, College of pharmacy, Guiyang 550025, China
^bZunyi Medical University, School of Pharmacy, Zunyi 563000, China

Received:2024-04-15 Revised:2024-05-08
Contact: ^*E-mail: huangqiang65@sina.com; yingzhou71@sina.com.
About author:^†These authors contributed equally to this work.
Supported by:
Guizhou Province Administration of Traditional Chinese Medicine Project (No.QZYY-2021-008).Chinese National Natural Science Foundation (No.82360679). Guizhou Provincial Basic Research Program(Natural Science) (QKHJC-ZK[2022] General 592).

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 were well-tolerated and afforded the desirable compounds in moderate to excellent yields (up to 92%). This reaction was 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 esters, Alcohols, NBS

Cite this article

Wang, Huabin, Xu, Lianhua, Liu, Xiongwei, Pan, Bowen, Yao, Zhen, Huang, Qiang, Zhou, Ying. NBS-Promoted Direct Phosphorylation of Alcohols with P(O)-H Compounds[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202403002.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Rodriguez, J. B.; GalloRodriguez, C. Chem. Med. Chem., 2019, 14, 190-216.
(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.
(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.
(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.
(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, 5786-5793.
(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, 1357-1361.
(b) Wang, W.-Y.; Jin, H.-G.; Yan, Z.-H.; He, M.-C.; Lin, S.; Tian, W.-S. Tetrahedron Lett. 2017, 58, 3489-3492.
[3] (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.)
[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, 1541-1547.
[6] Li C.-Y.; Chen T.-Q.; Han L.-B.Dalton Trans., 2016, 45, 14893-14897.
[7] Dhineshkumar J.; Prabhu K. R. Org. Lett., 2013, 15, 6062-6065
[8] Li Y.-J.; Yang Q.; Yang L.-Q.; Zheng K. Chem.Commun., 2019, 55, 4981-4984.
[9] (a) Zhong, W.-W.; Zhang, Q.; Li, M.-S.; Hu, D.-Y.; Cheng, M.; Du, F.-T.; Ji, J.-X.; Wei, W. Synthetic Communications, 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.
[10] (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.)
[11] Li Y.-J.; Liang F.-S.Tetrahedron Lett., 2016, 57, 2931-2934.
[12] (a) Li, Q.-Y.; Swaroop, T. R.; Hou, C.; Wang, Z.-Q.; Pan, Y.-M,; Tang, H.-T. Adv. Synth. Catal., 2019, 361, 1761-1765.
(b) Yu, X.-J.; Zhang, S.; Jiang, Z.-Y.; Zhang, H.-S.; Wang, T.-L. Eur. J. Org. Chem., 2020, 20, 3110-3113.
(c) Deng, L.-L.; Wang, Y.; Mei, H.-B.; Pan, Y.; Han, J.-L. J. Org. Chem., 2019, 84, 949-956.
(d) Tan, Y.-S.; Han, Y.-P.; Zhang, Y.-C.; Zhang, H.-Y.; Zhao, J.-Q,; Yang, S.-D. J. Org. Chem., 2022, 87, 3254-3264.
(e) Li, C.-J. Chin. J. Chem., 2022, 40, 838-845.
[13] (a) Huang, Y.-Y.; Wang, N.; Wu, Z.-G.; Wu, X.-X.; Wang, M.-K.; Huang, W.-C.; Zi, You. 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.)

[1]	Qishu Chen, Bo Yang, Qiwei Lang, Xiaobing Ding, Xiuxiu Li, Xumu Zhang. Ir/f-Amphox-Catalyzed Asymmetric Hydrogenation of 1-(Pyridin-2-yl)ketones to Chiral Pyridyl Alcohols^★ [J]. Chinese Journal of Organic Chemistry, 2025, 45(9): 3326-3334.
[2]	Youxue Zhao, Xiruo Li, Luobing Meng, Chunxiu Li, Guisheng Fan, Jianhe Xu. Advances in Understanding the Substrate Promiscuity of Alcohol Dehydrogenases/Carbonyl Reductases^★ [J]. Chinese Journal of Organic Chemistry, 2025, 45(9): 3175-3185.
[3]	Xiaoyan Wang, Changming Xu. Brønsted Acid-Catalyzed Primary Amination of Allylic Alcohols [J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 2932-2937.
[4]	Haochi Xie, Yongkang Qin, Ting Yang, Hujin Li, Jiajia Sun, Mingcheng Qian, Shuai Zhao, Ya'nan Hou, Xin Chen. Visible-Light-Mediated O—H Functionalization Reactions of Alkenyl Alcohols with Diazo Compounds [J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 3004-3016.
[5]	Liqiang Liu, Jun Nan, Xingyu Duan, Haolong Wang, Xiang Cai, Zicheng Wang, Enze Zhang, Yanmin Sun. N-Alkylation of Aliphatic Alcohol Amine Catalyzed by Tridentate P Ligand Ruthenium Complex [J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 2983-2988.
[6]	Shunli Du, Yaya Wang, Jiaming Guo, Xuewei Xu, Xinhua Peng. Study on the Borylation of β-C Positions of Aryl Olefins Catalyzed by Copper Organophosphorus Complexes [J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2435-2443.
[7]	Minhao Li, Zeming Wang, Qing Huang, Weiwei Zuo. Cobalt(II)-Catalyzed Asymmetric Hydrogen Transfer Reactions of Ketones [J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2451-2460.
[8]	Genhong Zhang, Ruoxi Yu, Yuegang Chen. Research Progress in Photo/Electro-Induced C(sp²)—C(sp³) Bond Construction by Activating C—O Bond of Alcohols and Their Derivatives [J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1548-1568.
[9]	Yulan Gao, Jiangqin Long, Qiusheng Wang. Properties Research of Poly(vinyl alcohol) Phosphorescent Films Doped with 9-Fluorenyl Methoxycarbonyl-Tyrosine at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1261-1267.
[10]	Xueying Yang, Yuanshuang Xu, Xinying Zhang, Xuesen Fan. Synthesis of C2-Spiroindolines Based on the Cascade Reaction of 2-Aryl-3H-indoles with Cyclopropanols [J]. Chinese Journal of Organic Chemistry, 2025, 45(2): 694-706.
[11]	Yuxia Liu, Congcong Li, Zhaoyang Fan, Qi Liu, Xinyu Dai. Isosteviol-Type Organocatalysts in Asymmetric Catalysis over the Past Decade [J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3613-3623.
[12]	Ying Li, Shuozhen Hu, Wei Fang, Xing Xiao, Xinsheng Zhang. Study on Synthesis of Glycine by Electrooxidation of Ethanolamine [J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3873-3884.
[13]	Yanyan Jiao, Feige Wang, Jian Xiao, Xiaode An. Recent Progress in the Dehydroxylative Functionalizations of Alcohols [J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3587-3612.
[14]	Shixiang Pan, Yan Liu, Zhuo Shi, Xingxing Lu, Yaoguo Qin, Cheng Qu, Chen Chen, Xinling Yang. Design, Synthesis and Bioactivity of Novel 2-Phenylethanol Ester Derivatives Containing Monoterpene Fragments [J]. Chinese Journal of Organic Chemistry, 2025, 45(1): 196-204.
[15]	Jinpeng Zhang, Yuliang Qian, Mengyan Ning, Tongqin Cai, Jingyao Su-Zhang, Quan Yu, Liangce Rong. α-Thiocyanation of Enol Acetates and Sodium Thiocyanate under Electrochemical Conditions [J]. Chinese Journal of Organic Chemistry, 2025, 45(1): 189-195.

NBS促进的P(O)-H化合物参与的醇的直接磷酸化反应

NBS-Promoted Direct Phosphorylation of Alcohols with P(O)-H Compounds

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments