Straightforward Solvent-Free Synthesis of Tertiary Phosphine Chalcogenides from Secondary Phosphines, Electron-Rich Alkenes, and Elemental Sulfur or Selenium
Corresponding Author
Alexander V. Artem'ev
Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033 Irkutsk, Russian Federation
Correspondence to: B. A. Trofimov; e-mail: [email protected].Search for more papers by this authorNataliya A. Chernysheva
Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033 Irkutsk, Russian Federation
Search for more papers by this authorSvetlana V. Yas'ko
Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033 Irkutsk, Russian Federation
Search for more papers by this authorNina K. Gusarova
Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033 Irkutsk, Russian Federation
Search for more papers by this authorIrina Yu Bagryanskaya
Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russian Federation
Novosibirsk State University, 630090 Novosibirsk, Russian Federation
Search for more papers by this authorCorresponding Author
Boris A. Trofimov
Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033 Irkutsk, Russian Federation
Correspondence to: B. A. Trofimov; e-mail: [email protected].Search for more papers by this authorCorresponding Author
Alexander V. Artem'ev
Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033 Irkutsk, Russian Federation
Correspondence to: B. A. Trofimov; e-mail: [email protected].Search for more papers by this authorNataliya A. Chernysheva
Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033 Irkutsk, Russian Federation
Search for more papers by this authorSvetlana V. Yas'ko
Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033 Irkutsk, Russian Federation
Search for more papers by this authorNina K. Gusarova
Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033 Irkutsk, Russian Federation
Search for more papers by this authorIrina Yu Bagryanskaya
Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russian Federation
Novosibirsk State University, 630090 Novosibirsk, Russian Federation
Search for more papers by this authorCorresponding Author
Boris A. Trofimov
Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033 Irkutsk, Russian Federation
Correspondence to: B. A. Trofimov; e-mail: [email protected].Search for more papers by this authorABSTRACT
A series of tertiary phosphine sulfides and selenides have been synthesized in excellent yields (88-99%) via a three-component reaction between secondary phosphines, electron-rich alkenes (styrene, vinyl chalcogenides), and elemental sulfur or selenium, proceeding under solvent-free conditions (80-82°C, 4–44 h). The interaction occurs via initial oxidation of secondary phosphines with elemental sulfur or selenium followed by noncatalyzed anti-Markovnikov addition of the generated R2P(E)H (E = S, Se) species to alkenes to afford the corresponding adducts with high chemo- and regioselectivity.
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