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

doi:10.6023/cjoc20203002

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (9): 2847-2853.DOI: 10.6023/cjoc20203002 Previous Articles Next Articles

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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

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贵州遵义 563000

收稿日期:2024-04-15 修回日期:2024-05-08 发布日期:2024-05-23
通讯作者: 黄强, 周英
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(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

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

a College of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025
b School of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563000

Received:2024-04-15 Revised:2024-05-08 Published:2024-05-23
Contact: Qiang Huang, Ying Zhou
About author:
^†These authors contributed equally to this work.
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)

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Abstract

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)

Cite this article

Huabin Wang, Lianhua Xu, Xiongwei Liu, Bowen Pan, Zhen Yao, Qiang Huang, Ying Zhou. N-Bromosuccinimide-Promoted Direct Phosphorylation of Alcohols with P(O)-H Compounds[J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2847-2853.

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Fig. & Tab. 6

References 13

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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

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

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Fig. & Tab. 6

References 13

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Entry	Additive	Solvent	Temp./℃	Yield^b/%
1	NBS	Toluene	25	69
2	NCS	Toluene	25	65
3	NIS	Toluene	25	61
4	NBS	CH₃CN	25	68
5	NBS	DMF	25	None
6	NBS	DMSO	25	None
7	NBS	DCM	25	92
8	NBS	EA	25	62
9	NBS	Dioxane	25	50
10	NBS	CS₂	25	73
11	NBS	Chloroform	25	86
12	NBS	CCl₄	25	87