Events The 13th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 13th International Electronic Conference on Synthetic Organic Chemistry

Published date

31 Oct, 2009

Citation

M. Reza Naimi-Jamal, Mehdi Farahmand, Zahra Karimi, Mohammad G. Dekamin, 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 International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2009, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-13-00194

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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

M. Reza Naimi-Jamal ¹

Mehdi Farahmand ¹

Zahra Karimi ¹

Mohammad G. Dekamin ¹

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

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