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Synthesis 2012(3): 431-438  
DOI: 10.1055/s-0031-1289655
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Nina K. Gusarova, Alexander V. Artem’ev, Ludmila A. Oparina, Nikita A. Kolyvanov, Svetlana F. Malysheva, Oksana V. Vysotskaya, Boris A. Trofimov*
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
Fax: +7(3952)419346; e-Mail: boris_trofimov@irioch.irk.ru;
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Publication History

Received 8 November 2011
Publication Date:
23 December 2011 (online)

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Abstract

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 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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