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Highly turnover number cyanosilylation of carbonyl compounds catalyzed by tetraethylammonium 2- (hydroxycarbamoyl)benzoate as a bifunctional organocatalyst: The role of hydrogen bonding
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1  Pharmaceutical and Biologically-Active Compounds Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran 16846-13114, Iran

Abstract: It was found that tetraethylammonium hydroxide reacts with N-hydroxyphthalimide as a nucleophile rather than a base to afford tetraethylammonium 2-(hydroxycarbamoyl)benzoate (TEAHCB). The TEAHCB was found to be able to efficiently catalyze the cyanosilylation of a wide range of carbonyl compounds as a bifunctional organocatalyst at very low catalyst loading (0.2 mol(percent)).
Keywords: Bifunctional organocatalysis; Cyanosilylation; tetraethylammonium (hydroxycarbamoyl)benzoate; Carbonyl compounds; Cyanohydrins; Hydrogen bonding