Mechanistic Study of the Recognition of the Aromatic SubstratesInduced by Weak Intermolecular Interaction within Lewis AcidCatalyst

摘要

The application of non-covalent interactions to organic syntheses is one of the mostpromising strategies for the development of efficient molecular transformations.1 Althoughmany chemoselective reactions have been developed by mimicking geometric and electronicstructures of enzymes,the recognition between simple carbon frameworks remains achallenging issue.2,3 Recently,we have reported the cage-shaped borates that can selectivelyactivate aromatic aldehydes prior to aliphatic ones with-pocket induced by three aryl groupsaround the boron center (borate 1a).4 When the cage-shaped borate had no π-pocket (borate1b),the selectivity was not observed.This aromatic selectivity would be driven by theinteraction between π-pocket and aromatic aldehydes.In order to gain further insights,weinvestigated the electronic and steric effects of aryl groups in borates.