Journal
CATALYSIS SCIENCE & TECHNOLOGY
Volume 2, Issue 7, Pages 1375-1381Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2cy20037f
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- Research Council of Iran University of Science and Technology (IUST), Iran [160/5295]
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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.
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