Details

Autor(en) / Beteiligte

• Aysin, Rinat R
• Galkin, Konstantin I

Titel

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

Ist Teil von

• Molecules (Basel, Switzerland), 2024-04, Vol.29 (8), p.1704

Ort / Verlag

Switzerland: MDPI AG

Erscheinungsjahr

2024

Quelle

EZB Electronic Journals Library

Beschreibungen/Notizen

• 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.