Synthesis of Functional Tripodal Phosphines with Amino and Ether Groups by the Hydrophosphination of Trivinyl Ethers with Secondary Phosphines

Ludmila A. Oparina; Nina K. Gusarova; Oksana V. Vysotskaya; Alexander V. Artem’ev; Nikita A. Kolyvanov; Boris A. Trofimov

doi:10.1055/s-0033-1340497

Synthesis, Table of Contents

Synthesis 2014; 46(05): 653-659
DOI: 10.1055/s-0033-1340497

paper

Synthesis of Functional Tripodal Phosphines with Amino and Ether Groups by the Hydrophosphination of Trivinyl Ethers with Secondary Phosphines

Ludmila A. Oparina

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Fax: +7(395)2419346 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(395)2419346 Email: boris_trofimov@irioch.irk.ru

,

Oksana V. Vysotskaya

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Fax: +7(395)2419346 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(395)2419346 Email: boris_trofimov@irioch.irk.ru

,

Nikita A. Kolyvanov

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Fax: +7(395)2419346 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(395)2419346 Email: boris_trofimov@irioch.irk.ru

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Abstract

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Abstract

A one-pot, atom-economic, metal- and halogen-free synthesis of functional triphosphines with nitrogen and (or) oxygen atoms as additional weaker coordinating sites (new hemilabile ligands) through exhaustive addition of secondary phosphines to available trivinyl ethers of aminotriols and triols has been developed. The reaction proceeds under free-radical conditions (UV irradiation or AIBN, with 3:1 reactant molar ratio) to give chemo- and regioselectively anti-Markovnikov triadducts to all three vinyloxy groups in good to excellent yields.

Key words

addition - alkenes - radical reaction - ligands - phosphorylation

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References

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