Highly Stereoselective Synthesis of 2,2-Disubstituted Vinylphosphonates via Aryl to Vinyl 1,4-Palladium Migration

被引:10
|
作者
Chen, Yan-Zhen [1 ]
Bao, Geng-Yu [1 ]
Zhan, Xin-Chen [1 ]
Fu, Jian-Guo [1 ]
Ji, Xiao-Ming [1 ]
Zhang, Shu-Sheng [1 ]
Feng, Chen-Guo [1 ]
机构
[1] Shanghai Univ Tradit Chinese Med, Res Ctr Chiral Drugs, Innovat Res Inst Tradit Chinese Med, Shanghai 201203, Peoples R China
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
1; 4-Palladium migration; Phosphorylation; C-H activation; Stereoselectivity; Cross-coupling; H-PHOSPHINE OXIDES; CATALYZED HYDROPHOSPHORYLATION; PALLADIUM; ALKYNES; ACIDS; BOND; 1,4-MIGRATION; BORYLATION; ACTIVATION; CHEMISTRY;
D O I
10.1002/cjoc.202200270
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Comprehensive Summary Vinylphosphates play an important role in the fields of synthetic chemistry, pharmaceuticals and material science. It is a long-standing challenge to control the geometry of multi-substituted vinylphosphates. Herein, an efficient method for the synthesis of 2,2-disubstituted vinylphosphonates has been reported. The reaction proceeded via aryl to vinyl 1,4-palladium migration progress, in which two difficulties that the deactivation of palladium catalyst by the coordination of excess secondary phosphine oxide and the competitive cross-coupling to form arylphosphonates are successfully overcome. The judicious selection of phosphine ligand is the key to success. This protocol features excellent regio- and stereoselectivitiy, generally excellent reaction yields and broad substrate socpe.
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收藏
页码:2188 / 2192
页数:5
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