Issue 7, 2009
From the journal:

Organic & Biomolecular Chemistry

The lithiation and acyl transfer reactions of phosphine oxides, sulfides and boranes in the synthesis of cyclopropanes†‡

Celia Clarke,a   David J. Fox,*b   Daniel Sejer Pedersenc  and  Stuart Warrena  

* Corresponding authors

a Cambridge University, University Chemical Laboratory, Lensfield Road, Cambridge, U.K.

b Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry, U.K
E-mail: d.j.fox@warwick.ac.uk

c University of Copenhagen, Department of Medicinal Chemistry, Universitetsparken 2, Copenhagen, Denmark

Abstract

Phosphine oxides are lithiated much faster than phosphine sulfides and phosphine boranes. Phosphine sulfides are in turn lithiated much more readily than phosphine boranes. It was possible to trap a phosphine sulfide THF in one case which upon treatment with t-BuOK gave cyclopropane, showing that phosphine sulfides readily undergo both phosphinoyl transfer and cyclopropane ring closure just like their phosphine oxide counterparts. The obtained data show that phosphine oxides are easily lithiated and undergo phosphoryl transfer much more readily and faster than phosphine sulfides and phosphine boranes. The observations suggest that it would be possible to perform reactions involving phosphine oxides in the presence of phosphine boranes or phosphine sulfides, potentially allowing regioselective alkylation of phosphine oxides in the presence of phosphine boranes or phosphine sulfides.

Graphical abstract: The lithiation and acyl transfer reactions of phosphine oxides, sulfides and boranes in the synthesis of cyclopropanes

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Article information

DOI
https://doi.org/10.1039/B817436A
Article type
Paper
Submitted
13 Oct 2008
Accepted
15 Jan 2009
First published
23 Feb 2009

Org. Biomol. Chem., 2009,7, 1329-1336

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The lithiation and acyl transfer reactions of phosphine oxides, sulfides and boranes in the synthesis of cyclopropanes

C. Clarke, D. J. Fox, D. S. Pedersen and S. Warren, Org. Biomol. Chem., 2009, 7, 1329 DOI: 10.1039/B817436A

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