Issue 37, 2012

Phosphine-boronates: efficient bifunctional organocatalysts for Michael addition

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

Supplementary files

Article information

Article type
Communication
Submitted
17 1 2012
Accepted
14 3 2012
First published
15 3 2012

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

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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