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Usage Statistics Cite this paper as: Dekamin, M.; Karimi, Z.; Farahmand, M.; Naimi-Jamal, M. Highly turnover number cyanosilylation of carbonyl compounds catalyzed by tetraethylammonium 2- (hydroxycarbamoyl)benzoate as a bifunctional organocatalyst: The role of hydrogen bonding. In Proceedings of the 13th Int. Electron. Conf. Synth. Org. Chem., 1-30 November 2009; Sciforum Electronic Conferences Series, 2009, a034:1-6.
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13th Int. Electron. Conf. Synth. Org. Chem. 2009, a034:1-6
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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
Pharmaceutical and Biologically-Active Compounds Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran 16846-13114, Iran;
* Author to whom correspondence should be addressed.
(This article belongs to the section A. General Organic Synthesis)
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
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