Catalyst- and Solvent-Free Stereoselective Addition of Secondary Phosphine Chalcogenides to Alkynes

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

doi:10.1055/s-0034-1379207

Synthesis, Table of Contents

Synthesis 2015; 47(02): 263-271
DOI: 10.1055/s-0034-1379207

paper

Catalyst- and Solvent-Free Stereoselective Addition of Secondary Phosphine Chalcogenides to Alkynes

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

,

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

,

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

,

Vladimir A. Shagun

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

,

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

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Abstract

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Abstract

The addition of secondary phosphine sulfides and selenides to alkynes proceeds readily (80 °C, 5–13 h) without catalysts or solvents to afford regio- and stereoselectively anti-Markovnikov adducts as tertiary alkenylphosphine chalcogenides of Z-configuration, in 60–94% yield.

Key words

addition reactions - alkynes - green chemistry - phosphine chalcogenides - regioselectivity

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References

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