General and chemoselective reduction of phosphine oxides by an enhanced oxophilic competition mechanism

被引:0
|
作者
You, Mengyao
Zhang, Ziwei
Chen, Chao
Mei, Zhichao
Zhang, Xinxin
Bai, Jiang
Huang, Haiyang [1 ]
Xiao, Qiang [1 ]
机构
[1] Jiangxi Sci & Technol Normal Univ, Jiangxi Prov Key Lab Organ Funct Mol, Nanchang 330013, Jiangxi Provinc, Peoples R China
基金
中国国家自然科学基金;
关键词
WITTIG REACTION; TERTIARY; ACID; APPEL; DERIVATIVES; CONVENIENT; MITSUNOBU; CATALYSIS; SECONDARY; LIGANDS;
D O I
10.1039/d5gc00477b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chemoselective reduction of phosphine oxides holds great significance for the preparation of phosphorus ligands and catalysts, as well as for the sustainable development of phosphorus chemistry. Previous approaches in this regard primarily involved the use of metal or custom-built catalysts, highly reactive and expensive reagents, or harsh conditions with deficient chemoselectivity. Here, we report an organocatalysis strategy for facile and efficient P 00000000 00000000 00000000 00000000 11111111 00000000 11111111 00000000 00000000 00000000 O reduction, utilizing only commercially available catalysts and inexpensive, mild silanes under mild reaction conditions. This approach demonstrates excellent chemoselectivity for preserving various easily reduced groups. Computational studies elucidate that the enhanced oxophilicity of catalytically generated electron-deficient silane species is crucial. Furthermore, scale-up investigations highlight potential applications in industrial recycling of phosphine oxides and straightforward preparation of novel phosphorus ligands.
引用
收藏
页码:3743 / 3750
页数:8
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