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Impact of Backbone Substitution on Organocatalytic Activity of Sterically Encumbered NHC in Benzoin Condensation

Authors :
Rinat R. Aysin
Konstantin I. Galkin
Source :
Molecules, Vol 29, Iss 8, p 1704 (2024)
Publication Year :
2024
Publisher :
MDPI AG, 2024.

Abstract

In this study, we provide a theoretical explanation for the experimentally observed decrease in the organocatalytic activity of N-aryl imidazolylidenes methylated at the C4/5-H positions in the benzoin condensation of aromatic aldehydes. A comparative quantum chemical study of energy profiles for the NHC-mediated benzoin condensation of furfural has revealed a high energy barrier to the formation of the IPrMe-based furanic Breslow intermediate that can be attributed to the negative steric interactions between the imidazole backbone methyl groups and N-aryl substituents.

Details

Language :
English
ISSN :
14203049
Volume :
29
Issue :
8
Database :
Directory of Open Access Journals
Journal :
Molecules
Publication Type :
Academic Journal
Accession number :
edsdoj.9fbdada715de4766a748ab000bb0bc81
Document Type :
article
Full Text :
https://doi.org/10.3390/molecules29081704