Variable mechanism of nucleophilic substitution of P-stereogenic phosphoryl chloride with alkynyl metallic reagents

被引：3

作者：

Yao, Lan ^{[1
]}

Liu, Li-Juan ^{[1
]}

Xu, Zhong-Yuan ^{[1
]}

Nie, Shao-Zhen ^{[1
]}

Xiao, Xiao-Qing ^{[1
]}

Zhao, Chang-Qiu ^{[1
]}

机构：

[1] Liaocheng Univ, Coll Chem & Chem Engn, Liaocheng 252059, Shandong, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 05期

关键词：

PALLADIUM-CATALYZED SYNTHESIS; TERMINAL ALKYNES; H-PHOSPHONATES; EFFICIENT; BIARYLS; ETHOXIDE; LIGANDS; OXIDES; BOND;

D O I：

10.1039/c5ob01871d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The variable mechanism for substitution of P-stereogenic phosphoryl chloride with alkynyl metallic reagents, which depends on temperature, stoichiometry of starting materials, and the structure of the nucleophilic reagent, is assumed as either S(N)2-like or Berry pseudorotation of pentacoordinated phosphorus intermediates, affording inversion and retention products, respectively. The formation of the inversion product can be controlled to occur predominantly to afford (RP)-alkynylphosphinates.

引用

页码：1702 / 1706

页数：5

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