A Simple synthesis of vinylphosphonates from dialkyl(aryl) phosphites and alkyl(aryl) propiolates in aqueous acetone

Subject Areas :

Maryam Adlu ¹ , Issa Yavari ² , Javad Azizian ³

1 - Chemistry Department, Science and Research Branch, Islamic Azad University Tehran, IRAN.
2 - Chemistry Department, Science and Research Branch, Islamic Azad University Tehran, IRAN.
3 - Chemistry Department, Science and Research Branch, Islamic Azad University Tehran, IRAN.

Received: 2022-11-10 Accepted : 2022-12-04 Published : 2022-12-01

Keywords: Alkyl(aryl) propiolates, Dialkyl(aryl) phosphites, Vinylphosphonates, Sodium cyanide,

Abstract :

In this work, simple and mild efficient synthesis of various organophosphorus compounds based on the reaction of dialkyl(aryl) phosphites with alkyl(aryl) propiolates in the presence of NaCN in aqueous acetone, is described. Organophosphorus compounds are widely used in organic synthesis, such as agricultural chemicals, flame retardants, medicinal agents and the preparation of insecticides. Using this approach, to a solution of alkyl(aryl) propiolates and dialkyl(aryl) phosphite was added sodium cyanide in acetone/H2O at room temperature, and the solution was stirred. The solvent was removed under reduced pressure, and the residue was dissolved in EtOAc, washed with aqueous NaHCO3 and brine, dried (Na2SO4), and the solvent was removed under reduced pressure. The crude product was purified by flash column chromatography on silica gel using n-hexane-EtOAc as eluent. Then, All organophosphorus compounds are obtained in excellent yields. The method offers several advantages including operational simplicity, high diversity via various functional groups and fairly good yields.