Three-Component Reaction between Vinyl Ethers, Secondary Phosphines, and Elemental Selenium: One-Pot Synthesis of 1-(Alkoxy)ethyl and 1-(Aryloxy)ethyl Phosphinodiselenoates

Abstract

A family of previously unknown phosphinodiselenoic esters containing a selenoacetal moiety, R^² ₂P(=Se)SeCH(Me)OR^¹ (R^¹, R^² = alkyl, aryl, etc.), were synthesized by means of a three-component reaction between the elemental selenium and the corresponding vinyl ether and secondary phosphine. The reaction proceeds readily in 1,4-dioxane at 90 ˚C for 1-1.5 hours and gives the phosphinodiselenoic esters quantitatively and in an entirely atom-economic manner. The reaction proceeds through electrophilic addition to the electron-rich double bond of the phosphinodiselenoic acids generated in situ.

Key words

phosphines - multicomponent reactions - phosphorus - selenium - phosphinodiselenoate esters

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