Aerobic addition of secondary phosphine oxides to vinyl sulfides: a shortcut to 1-hydroxy-2-(organosulfanyl)ethyl(diorganyl)phosphine oxides

Svetlana F Malysheva; Alexander V Artem'ev; Nina K Gusarova; Nataliya A Belogorlova; Alexander I Albanov; C W Liu; Boris A Trofimov

doi:10.3762/bjoc.11.214

Aerobic addition of secondary phosphine oxides to vinyl sulfides: a shortcut to 1-hydroxy-2-(organosulfanyl)ethyl(diorganyl)phosphine oxides

Beilstein J Org Chem. 2015 Oct 23:11:1985-90. doi: 10.3762/bjoc.11.214. eCollection 2015.

Authors

Svetlana F Malysheva¹, Alexander V Artem'ev¹, Nina K Gusarova¹, Nataliya A Belogorlova¹, Alexander I Albanov¹, C W Liu², Boris A Trofimov¹

Affiliations

¹ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation.
² Department of Chemistry, National Dong Hwa University, Hualien 97401, Taiwan.

Abstract

Secondary phosphine oxides react with vinyl sulfides (both alkyl- and aryl-substituted sulfides) under aerobic and solvent-free conditions (80 °C, air, 7-30 h) to afford 1-hydroxy-2-(organosulfanyl)ethyl(diorganyl)phosphine oxides in 70-93% yields.

Keywords: addition; green method; phosphine oxides; regioselectivity; vinyl sulfides.