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

A family of previously unknown phosphinodiselenoic esters containing a selenoacetal moiety, R² ₂P(=Se)SeCH(Me)OR¹ (R¹, R² = 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 atomeconomic manner. The reaction proceeds through electrophilic addition to the electron-rich double bond of the phosphinodiselenoic acids generated in situ. [ABSTRACT FROM AUTHOR]