Unprecedented Control of Selectivity in Nickel-Catalyzed Hydrophosphorylation of Alkynes: Efficient Route to Monoand Bisphosphonates

被引：60

作者：

Khemchyan, Levon L. ^{[1
]}

Ivanova, Julia V. ^{[1
]}

Zalesskiy, Sergey S. ^{[1
]}

Ananikov, Valentine P. ^{[1
]}

Beletskaya, Irina P. ^{[2
]}

Starikova, Zoya A. ^{[3
]}

机构：

[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia

[2] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119899, Russia

[3] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 04期

基金：

俄罗斯基础研究基金会;

关键词：

alkynes; homogeneous catalysis; nickel; phosphorylation; selectivity; METABOTROPIC GLUTAMATE RECEPTORS; P-H BOND; TERMINAL ALKYNES; CONJUGATE ADDITION; P(O)-H BONDS; C-P; METAL; PHOSPHONATES; ACID; MECHANISMS;

D O I：

10.1002/adsc.201400123

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A unique nickel-based catalytic system was developed where the direction of the hydrophosphorylation reaction can be controlled by varying the catalyst loading. A flexible one-pot access to vinylmonophosphonates and alkylbisphosphonates was demonstrated using simple starting materials in an atom-economic reaction without any specific solvents or ligands. Monitoring of the reaction mechanism with joint NMR and MS studies revealed key information about the reaction intermediates. The synthetic scope of the developed catalytic system was explored and the utility of the synthesized products for the fire protection of cotton materials was demonstrated.

引用

页码：771 / 780

页数：10

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