Benzoin condensation of aromatic aldehydes catalyzed by N-heterocyclic carbenes under mild conditions | European Journal of Chemistry

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Published: Mar 31, 2019

DOI: https://doi.org/10.5155/eurjchem.10.1.1-6.1826

Keywords:

Aldehydes, Heterocycles, Organocatalysis, Room temperature, Benzoin condensation, N-heterocyclic carbenes

Section

Research Article

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Vol. 10 No. 1 (2019): March 2019

Dates

Received 2018-12-13
Accepted 2019-01-08
Published 2019-03-31

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Isabel Monreal-Leyva

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Department of Chemistry, University of Nebraska at Kearney, Kearney, NE, 68849, USA

http://orcid.org/0000-0002-7270-7502

Breanna Rose Attema

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Department of Chemistry, University of Nebraska at Kearney, Kearney, NE, 68849, USA

http://orcid.org/0000-0002-5231-9430

Nuri Bae

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Department of Chemistry, University of Nebraska at Kearney, Kearney, NE, 68849, USA

Haishi Cao

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Department of Chemistry, University of Nebraska at Kearney, Kearney, NE, 68849, USA

http://orcid.org/0000-0002-6789-0998

Hector Palencia

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Department of Chemistry, University of Nebraska at Kearney, Kearney, NE, 68849, USA

http://orcid.org/0000-0001-8634-8232

Abstract

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.

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Monreal-Leyva, I.; Attema, B. R.; Bae, N.; Cao, H.; Palencia, H. Benzoin Condensation of Aromatic Aldehydes Catalyzed by N-Heterocyclic Carbenes under Mild Conditions. Eur. J. Chem. 2019, 10, 1-6.

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