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Benzoin condensation of aromatic aldehydes catalyzed by N-heterocyclic carbenes under mild conditions
Isabel Monreal-Leyva (1)
, Breanna Rose Attema (2) , Nuri Bae (3) , Haishi Cao (4) , Hector Palencia (5,*) (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.
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DOI: 10.5155/eurjchem.10.1.1-6.1826
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Citations
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DOI: 10.1021/acs.organomet.2c00171
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