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

doi:10.6023/cjoc202405043

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (12): 3747-3752.DOI: 10.6023/cjoc202405043 Previous Articles Next Articles

ARTICLE

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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Abstract

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

Cite this article

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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Fig. & Tab. 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

References 36

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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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Fig. & Tab. 7

References 36

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