Highly turnover number cyanosilylation of carbonyl compounds catalyzed by tetraethylammonium 2- (hydroxycarbamoyl)benzoate as a bifunctional organocatalyst: The role of hydrogen bonding

M. Reza Naimi-Jamal; Mehdi Farahmand; Zahra Karimi; Mohammad Dekamin

doi:10.3390/ecsoc-13-00194

Previous Article in event

Dual Proline/Water Compatible Lewis Acid Activation: a Biomimetic Approach for Direct Asymmetric Aldol Reaction

Next Article in event

Synthesis and characterization of zeolite-encapsulated porphyrins

Highly turnover number cyanosilylation of carbonyl compounds catalyzed by tetraethylammonium 2- (hydroxycarbamoyl)benzoate as a bifunctional organocatalyst: The role of hydrogen bonding

M. Reza Naimi-Jamal

Mehdi Farahmand

Zahra Karimi

Mohammad G. Dekamin

¹ Pharmaceutical and Biologically-Active Compounds Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran 16846-13114, Iran

Published: 31 October 2009 by MDPI in The 13th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-13-00194

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

View paper View Poster

50 Reads
0 Recommendations

M. Reza Naimi-Jamal

Mehdi Farahmand

Zahra Karimi

Mohammad Dekamin