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Benzoin condensation of aromatic aldehydes catalyzed by N-heterocyclic carbenes under mild conditions Monreal-Leyva, Isabel Attema, Breanna Rose Bae, Nuri Cao, Haishi Palencia, Hector Aldehydes Heterocycles Organocatalysis Room temperature Benzoin condensation N-heterocyclic carbenes The benzoin condensation was used to evaluate the catalytic activity of different N-heterocyclic carbenes as a function of their structure and N-substituents. There is a correlation between the length of an N-alkyl substituent and its performance as an organocatalyst. Heteroaromatic aldehydes were found to be the most reactive, among the screened substrates, finishing the reaction in 30 minutes, with almost quantitative yields. On the other hand, p-nitrobenzaldehyde, a strongly electrophilic aldehyde, was the least reactive. Electronic effects have little influence on the reaction yield but steric effects can dramatically reduce it. The preformed organocatalyst reacts faster than the generated in situ, with minimum solvent. Atlanta Publishing House LLC 2019-03-31 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion application/pdf https://www.eurjchem.com/index.php/eurjchem/article/view/1826 10.5155/eurjchem.10.1.1-6.1826 European Journal of Chemistry; Vol. 10 No. 1 (2019): March 2019; 1-6 2153-2257 2153-2249 eng https://www.eurjchem.com/index.php/eurjchem/article/view/1826/pdf_1826 Copyright (c) 2019 Authors