烯基锍盐脱硫构建C—P键合成末端乙烯基膦氧化物

doi:10.6023/cjoc202405043

有机化学 ›› 2024, Vol. 44 ›› Issue (12): 3747-3752.DOI: 10.6023/cjoc202405043 上一篇下一篇

研究论文

烯基锍盐脱硫构建C—P键合成末端乙烯基膦氧化物

安江振^a, 吕琪妍^a^,^b, 孙凯^a^,^*(), 陈晓岚^a, 屈凌波^a, 於兵^a^,^*()

a 郑州大学化学学院郑州 450001
b 南京林业大学江苏省林业资源高效加工利用协同创新中心南京 210037

收稿日期:2024-05-29 修回日期:2024-07-20 发布日期:2024-08-16
基金资助:
国家自然科学基金(22171249); 国家自然科学基金(22071222)

Synthesis of Terminal Vinyl Phosphine Oxides via Desulfonative C—P Formation from Alkenyl Sulfonium Salts

Jiangzhen An^a, Qiyan Lv^a^,^b, Kai Sun^a^,^*(), Xiaolan Chen^a, Lingbo Qu^a, Bing Yu^a^,^*()

a College of Chemistry, Zhengzhou University, Zhengzhou 450001
b Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037

Received:2024-05-29 Revised:2024-07-20 Published:2024-08-16
Contact: *E-mail:sunkaichem@zzu.edu.cn;bingyu@zzu.edu.cn
Supported by:
National Natural Science Foundation of China(22171249); National Natural Science Foundation of China(22071222)

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摘要/Abstract

以碳酸铯为碱, 在室温下实现了烯基锍盐和膦氧化物的脱硫反应, 构筑C(sp²)—P键. 该方法具有操作简单、反应温和及官能团兼容性强等特点, 为合成末端乙烯基膦氧化物提供了简单、高效的制备手段.

关键词: 脱硫偶联, 乙烯基膦氧化物, 碳-磷键, 烯基锍盐

Cesium carbonate was used as a base to achieve the desulfurization reaction of alkenyl sulfonium salts and phosphine oxides at room temperature, forming C(sp²)—P bonds. This method features simple operation, mild reaction conditions, and good functional group compatibility, offering a straightforward and efficient preparation route for terminal vinyl phosphine oxides.

Key words: desulfonative coupling, vinyl phosphine oxide, C—P bond, alkenyl sulfonium salt

引用此文

安江振, 吕琪妍, 孙凯, 陈晓岚, 屈凌波, 於兵. 烯基锍盐脱硫构建C—P键合成末端乙烯基膦氧化物[J]. 有机化学, 2024, 44(12): 3747-3752.

Jiangzhen An, Qiyan Lv, Kai Sun, Xiaolan Chen, Lingbo Qu, Bing Yu. Synthesis of Terminal Vinyl Phosphine Oxides via Desulfonative C—P Formation from Alkenyl Sulfonium Salts[J]. Chinese Journal of Organic Chemistry, 2024, 44(12): 3747-3752.

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图/表 7

Scheme 1. Synthesis of terminal vinyl phosphine oxides

Entry	Solvent	Base	Time/h	Yield^b/%
1	THF	Cs₂CO₃	3	32
2	MeCN	Cs₂CO₃	3	83
3	DMSO	Cs₂CO₃	3	11
4	H₂O	Cs₂CO₃	3	15
5	DCM	Cs₂CO₃	3	72
6	MeCN	K₃PO₄	3	44
7	MeCN	K₂CO₃	3	65
8	MeCN	DBU	3	trace
9	MeCN	Cs₂CO₃	6	75
10	MeCN	Cs₂CO₃	1	81

Table 1. Optimization of reaction conditionsa

Scheme 2. Scope of phosphine oxides

Scheme 3. Scope of vinyl sulfonium salts

Scheme 4. Gram-scale synthesis

Scheme 5. Control experiments

Scheme 6. Proposed mechanism

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烯基锍盐脱硫构建C—P键合成末端乙烯基膦氧化物

Synthesis of Terminal Vinyl Phosphine Oxides via Desulfonative C—P Formation from Alkenyl Sulfonium Salts

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