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Issue 2, 2010
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A straightforward synthesis of unsymmetrical secondary phosphine boranes

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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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Publication details

The article was received on 29 Sep 2009, accepted on 11 Nov 2009 and first published on 14 Jan 2010


Article type: Paper
DOI: 10.1039/B920324A
Citation: 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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