In this study, we provide a theoretical explanation for the experimentally observed decrease in the organocatalytic activity of -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 IPr-based furanic Breslow intermediate that can be attributed to the negative steric interactions between the imidazole backbone methyl groups and -aryl substituents.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11051995 | PMC |
| http://dx.doi.org/10.3390/molecules29081704 | DOI Listing |
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