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Issue 7, 2012
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Tetraethylammonium 2-(N-hydroxycarbamoyl)benzoate: a powerful bifunctional metal-free catalyst for efficient and rapid cyanosilylation of carbonyl compounds under mild conditions

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Abstract

In contrast to tetrabutylammonium hydroxide, its tetraethylammonium counterpart reacts with N-hydroxyphthalimide to afford tetraethylammonium 2-(N-hydroxycarbamoyl)benzoate (TEAHCB) rather than tetraethylammonium phthalimide-N-oxyl (TEAPINO). TEAHCB contains at the same time benzoate and hydroxycarbamoyl functionalities in a proper geometry to activate reaction components as Lewis basic and Lewis acidic centers, respectively. TEAHCB was found to be able to efficiently catalyze very rapid cyanosilylation of a wide variety of carbonyl compounds at 0.15 mol% catalyst loading under solvent-free conditions at room temperature as a simple and readily available bifunctional organocatalyst.

Graphical abstract: Tetraethylammonium 2-(N-hydroxycarbamoyl)benzoate: a powerful bifunctional metal-free catalyst for efficient and rapid cyanosilylation of carbonyl compounds under mild conditions

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Publication details

The article was received on 20 Jan 2012, accepted on 17 Mar 2012 and first published on 20 Mar 2012


Article type: Paper
DOI: 10.1039/C2CY20037F
Catal. Sci. Technol., 2012,2, 1375-1381

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    Tetraethylammonium 2-(N-hydroxycarbamoyl)benzoate: a powerful bifunctional metal-free catalyst for efficient and rapid cyanosilylation of carbonyl compounds under mild conditions

    M. G. Dekamin, Z. Karimi and M. Farahmand, Catal. Sci. Technol., 2012, 2, 1375
    DOI: 10.1039/C2CY20037F

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