Phosphine-boronates: efficient bifunctional organocatalysts for Michael addition

Olivier Baslé; Susana Porcel; Sonia Ladeira; Ghenwa Bouhadir; Didier Bourissou

doi:10.1039/C2CC30399J

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Chemical Communications

Issue 37, 2012

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Phosphine-boronates: efficient bifunctional organocatalysts for Michael addition

Olivier Baslé,^a^b Susana Porcel,^a^b Sonia Ladeira,^c Ghenwa Bouhadir*^a^b and Didier Bourissou*^a^b

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

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

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

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

DOI: 10.1039/C2CC30399J
Received 17 Jan 2012, Accepted 14 Mar 2012
First published online 15 Mar 2012

This article is part of themed collection: Frontiers in Molecular Main Group Chemistry

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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.

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Olivier Baslé
Susana Porcel
Sonia Ladeira
Ghenwa Bouhadir
Didier Bourissou

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