Issue 2, 2010
From the journal:

Green Chemistry

A straightforward synthesis of unsymmetrical secondary phosphine boranes†

Christelle Petit,a   Alain Favre-Réguillon,*ab   Gérard Mignanic  and  Marc Lemaire*a  

* Corresponding authors

a Laboratoire de Catalyse et de Synthèse Organique, UMR 5246, ICBMS, Université Claude Bernard Lyon 1, CPE Bat. 308, 43, bd du 11 Novembre 1918, Villeurbanne, Cedex, France
E-mail: marc.lemaire@univ lyon1.fr

b Laboratoire de Transformations Chimiques et Pharmaceutiques, Conservatoire National des Arts et Métiers, 2 rue Conté, Paris, France
E-mail: alain.favre-reguillon@univ-lyon1.fr

c Rhodia, Lyon Research Center, 85, avenue des Frères Perret, BP 62, Saint-Fons, Cedex, France

Abstract

A one-pot procedure for the synthesis of unsymmetrical alkyl-substituted secondary phosphine oxides is described. The sequential addition of N-benzylaniline to a solution of dichlorophenylphosphine and 1-methylimidazole in methylcyclohexane, separating of the protic ionic liquid formed, addition of Grignard reagent followed by hydrolysis gave unsymmetrical secondary phosphine oxides (SPOs) in high yield. The use of ionic liquids in the first step is essential and streamlined the synthesis. Unsymmetrical SPOs could be quantitatively reduced to secondary phosphine using a catalytic amount of Ti(OiPr)4 and tetramethyldisiloxane (TMDS) under mild reaction conditions.

Graphical abstract: A straightforward synthesis of unsymmetrical secondary phosphine boranes

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Article information

DOI
https://doi.org/10.1039/B920324A
Article type
Paper
Submitted
29 Sep 2009
Accepted
11 Nov 2009
First published
14 Jan 2010

Green Chem., 2010,12, 326-330

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A straightforward synthesis of unsymmetrical secondary phosphine boranes

C. Petit, A. Favre-Réguillon, G. Mignani and M. Lemaire, Green Chem., 2010, 12, 326 DOI: 10.1039/B920324A

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