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

来源：

CHINESE JOURNAL OF CHEMISTRY | 2022年 / 40卷 / 18期

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.

引用

页码：2188 / 2192

页数：5