Catalyst-Free and Solvent-Free Addition of P(Se)–H Species to Alkenes: A Straightforward Access to Tertiary Phosphine Selenides

Svetlana F. Malysheva; Nina K. Gusarova; Alexander V. Artem’ev; Nataliya A. Belogorlova; Alexander I. Albanov; Tatyana N. Borodina; Vladimir I. Smirnov; Boris A. Trofimov

doi:10.1055/s-0034-1378357

Synthesis, Table of Contents

Synthesis 2014; 46(19): 2656-2662
DOI: 10.1055/s-0034-1378357

paper

Catalyst-Free and Solvent-Free Addition of P(Se)–H Species to Alkenes: A Straightforward Access to Tertiary Phosphine Selenides

Authors

Svetlana F. Malysheva

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033, Irkutsk, Russian Federation Fax: +7(3952)419346 Email: boris_trofimov@irioch.irk.ru
Nina K. Gusarova

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033, Irkutsk, Russian Federation Fax: +7(3952)419346 Email: boris_trofimov@irioch.irk.ru
Alexander V. Artem’ev

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033, Irkutsk, Russian Federation Fax: +7(3952)419346 Email: boris_trofimov@irioch.irk.ru
Nataliya A. Belogorlova

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033, Irkutsk, Russian Federation Fax: +7(3952)419346 Email: boris_trofimov@irioch.irk.ru
Alexander I. Albanov

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033, Irkutsk, Russian Federation Fax: +7(3952)419346 Email: boris_trofimov@irioch.irk.ru
Tatyana N. Borodina

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033, Irkutsk, Russian Federation Fax: +7(3952)419346 Email: boris_trofimov@irioch.irk.ru
Vladimir I. Smirnov

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033, Irkutsk, Russian Federation Fax: +7(3952)419346 Email: boris_trofimov@irioch.irk.ru
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 Email: boris_trofimov@irioch.irk.ru

Abstract

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Abstract

Under catalyst- and solvent-free conditions, secondary phosphine selenides easily add to diverse alkenes [acrylonitrile, allyl alcohol, styrene, vinyl ethers, vinyl sulfides, and trimethyl(vinyl)silane] at 80 °C (3–20 h) to give anti-Markovnikov adducts in 70–95% yield.

Key words

addition - alkenes - green method - phosphine selenides - regioselectivity

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References

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Supplementary Material

Supporting Information (PDF)