European Journal of Chemistry 2019, 10(1), 1-6 | doi: https://doi.org/10.5155/eurjchem.10.1.1-6.1826 | Get rights and content

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Benzoin condensation of aromatic aldehydes catalyzed by N-heterocyclic carbenes under mild conditions


Isabel Monreal-Leyva (1) orcid , Breanna Rose Attema (2) orcid , Nuri Bae (3) , Haishi Cao (4) orcid , Hector Palencia (5,*) orcid

(1) Department of Chemistry, University of Nebraska at Kearney, Kearney, NE, 68849, USA
(2) Department of Chemistry, University of Nebraska at Kearney, Kearney, NE, 68849, USA
(3) Department of Chemistry, University of Nebraska at Kearney, Kearney, NE, 68849, USA
(4) Department of Chemistry, University of Nebraska at Kearney, Kearney, NE, 68849, USA
(5) Department of Chemistry, University of Nebraska at Kearney, Kearney, NE, 68849, USA
(*) Corresponding Author

Received: 13 Dec 2018 | Revised: 05 Jan 2019 | Accepted: 08 Jan 2019 | Published: 31 Mar 2019 | Issue Date: March 2019

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.


Keywords


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

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DOI: 10.5155/eurjchem.10.1.1-6.1826

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Research Corporation for Science Advancement.

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How to cite


Monreal-Leyva, I.; Attema, B.; Bae, N.; Cao, H.; Palencia, H. Eur. J. Chem. 2019, 10(1), 1-6. doi:10.5155/eurjchem.10.1.1-6.1826
Monreal-Leyva, I.; Attema, B.; 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), 1-6. doi:10.5155/eurjchem.10.1.1-6.1826
Monreal-Leyva, I., Attema, B., Bae, N., Cao, H., & Palencia, H. (2019). Benzoin condensation of aromatic aldehydes catalyzed by N-heterocyclic carbenes under mild conditions. European Journal of Chemistry, 10(1), 1-6. doi:10.5155/eurjchem.10.1.1-6.1826
Monreal-Leyva, Isabel, Breanna Rose Attema, Nuri Bae, Haishi Cao, & Hector Palencia. "Benzoin condensation of aromatic aldehydes catalyzed by N-heterocyclic carbenes under mild conditions." European Journal of Chemistry [Online], 10.1 (2019): 1-6. Web. 18 May. 2022
Monreal-Leyva, Isabel, Attema, Breanna, Bae, Nuri, Cao, Haishi, AND Palencia, Hector. "Benzoin condensation of aromatic aldehydes catalyzed by N-heterocyclic carbenes under mild conditions" European Journal of Chemistry [Online], Volume 10 Number 1 (31 March 2019)

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