Synthesis 2014; 46(05): 653-659
DOI: 10.1055/s-0033-1340497
paper
© Georg Thieme Verlag Stuttgart · New York

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
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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
› Author Affiliations
Further Information

Publication History

Received: 17 October 2013

Accepted after revision: 09 December 2013

Publication Date:
08 January 2014 (online)


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.

Supporting Information