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

Authors

  • 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
Further Information

Publication History

Received: 17 October 2013

Accepted after revision: 09 December 2013

Publication Date:
08 January 2014 (online)


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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.

Supporting Information