Synthesis of diphenylphosphinic acid esters

Ewelina Korzeniowska

doi:10.17951/aa.2017.72.1.23

Abstract

<p>The development of new methods for the synthesis of organophosphorus compounds is still an important part of organic chemistry due to the high demand for these compounds in organic synthesis as well as in asymmetric catalysis. Most of the methods for the synthesis of these compounds include the reactivity of the phosphorus atom, which depending on the structure might exhibit both electrophilic and nucleophilic properties. Herein, I will present the results concerning synthesis of diphenylphosphinic acid esters.</p>

Highlights

The development of new methods for the synthesis of organophosphorus compounds is still an important part of organic chemistry due to the high demand for these compounds in organic synthesis as well as in asymmetric catalysis
Most of the methods for the synthesis of these compounds include the reactivity of the phosphorus atom, which depending on the structure might exhibit both electrophilic and nucleophilic properties
The phosphorus compounds having alkoxy groups bonded to the phosphorus atom are excellent substrates for the synthesis of various types of organophosphorus-compounds

Summary

INTRODUCTION

The development of new methods for the synthesis of organophosphorus compounds is still an important part of organic chemistry due to the high demand for these compounds in organic synthesis as well as in asymmetric catalysis. Oshiki and Imamoto explored the nucleophilic substitution reaction of optically pure methylphenylphosphinous acidborane methyl ester with organolithium reagents [5] These results demonstrated that less sterically hindered reagents such as m-anisyllithium or p-anisyllithium react with substrate to afford the corresponding products with inversion of configuration, but o-substituted phenyllithium reagents lead to the substitution product with low enantiomeric excess. Jugé and co-workers described the asymmetric synthesis of mono- and diphosphines based on the nucleophilic substitution reaction of 1,1’-dilithioferrocene with two equivalents of oxazaphospholidine-borane [11]. This approach led to the desired product with only 10% yield. To summarize phosphinic esters are very important starting materials and intermediates in organophosphorus chemistry

General

General procedure for the synthesis of diphenylphosphinic acid esters

AND DISCUSSION

CONCLUSIONS