One-Pot Vinylation of Secondary Phosphine Chalcogenides with Vinyl Sulfoxides

Svetlana F. Malysheva A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia

Nina K. Gusarova A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia

Natal'ya A. Belogorlova A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia

Tamara V. Kashik A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia

Leonid B. Krivdin A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia

Sergei V. Fedorov A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia

Boris A. Trofimov A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia

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Abstract

A facile, one-pot vinylation of secondary phosphine chalcogenides with alkyl(or aryl) vinyl sulfoxides has been elaborated. The vinylation comprises the nucleophilic addition of secondary phosphine chalcogenides to the vinyl sulfoxides (∼50 mol% KOH, dioxane, 25–40°C, 1 h) followed by the elimination of sulfenic acids from the adducts (additional equivalent of KOH, 60–70°C, 1.5–2.0 h), the yields of target tertiary vinyl phosphine chalcogenides reaching 92%.

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Acknowledgments

Financial support from the Russian Foundation for Basic Research (grants no. 07-03-00562 and 08-03-00021) is gratefully acknowledged.

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One-Pot Vinylation of Secondary Phosphine Chalcogenides with Vinyl Sulfoxides

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One-Pot Vinylation of Secondary Phosphine Chalcogenides with Vinyl Sulfoxides

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