Issue 37, 2012
From the journal:

Chemical Communications

Phosphine-boronates: efficient bifunctional organocatalysts for Michael addition†‡

Olivier Baslé,§ab   Susana Porcel,ab   Sonia Ladeira,c   Ghenwa Bouhadir*ab  and  Didier Bourissou*ab  

* Corresponding authors

a Université de Toulouse, UPS, LHFA, 118 route de Narbonne, F-31062 Toulouse, France
E-mail: dbouriss@chimie.ups-tlse.fr

b CNRS, LHFA UMR 5069, F-31062 Toulouse, France
Fax: +33 5 6155 8204
Tel: +33 5 6155 6803

c Université Paul Sabatier, Institut de Chimie de Toulouse (FR 2599), 118 route de Narbonne, 31062 Toulouse Cedex 9, France

Abstract

Phosphine-boronates R2P(o-C6H4)B(OR′)2 have been evaluated as bifunctional organocatalysts for the Michael addition of malonate pronucleophiles to methylvinylketone. The presence of the Lewis acidic boron center adjacent to phosphorus significantly improves catalytic performance. Isolation and complete characterization of a key intermediate, namely a β-phosphonium enolate, substantiate the role of the Lewis acidic moiety in the catalytic process.

Graphical abstract: Phosphine-boronates: efficient bifunctional organocatalysts for Michael addition

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Article information

DOI
https://doi.org/10.1039/C2CC30399J
Article type
Communication
Submitted
17 Jan 2012
Accepted
14 Mar 2012
First published
15 Mar 2012

Chem. Commun., 2012,48, 4495-4497

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Phosphine-boronates: efficient bifunctional organocatalysts for Michael addition

O. Baslé, S. Porcel, S. Ladeira, G. Bouhadir and D. Bourissou, Chem. Commun., 2012, 48, 4495 DOI: 10.1039/C2CC30399J

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