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Synthesis 2008(19): 3121-3125  
DOI: 10.1055/s-2008-1067275
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Convenient Mild and Selective Hydrophosphination of Functionalized Alkenes: Access to P,O and P,S Derivatives

Benoit Join, Jean-François Lohier, Olivier Delacroix, Annie-Claude Gaumont*
Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen Basse-Normandie, CNRS, 6 boulevard du Maréchal Juin, 14050 Caen, France
Fax: +33(2)31452877; e-Mail: annie-claude.gaumont@ensicaen.fr;
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Publication History

Received 2 May 2008
Publication Date:
05 September 2008 (online)

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Abstract

The synthesis of new functionalized phosphines is carried out through the easy and atom economic hydrophosphination reaction of functionalized alkenes such as vinyl ethers and vinyl thioethers. The reactions occur under mild conditions without catalyst using phosphine-boranes as hydrophosphinating agents.

Key words

addition reactions - alkenes - boron - phosphorus - radical reactions

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7

Transfer of the borane group from a phosphorus to an oxygen atom was already mentioned in the literature: see ref. 6.

12

With a simple alkene such as oct-1-ene, the hydrophos­-phination could be carried out at 80 ˚C without any decomplexation and oxidative side reactions (see ref. 3b).