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A pH-Switchable Electrostatic Catalyst for the Diels-Alder Reaction: Progress toward Synthetically Viable Electrostatic Catalysis

Blyth, Mitchell; Coote, Michelle


Density functional theory calculations at the SMD/M06-2X/6-31+G(d,p)//M06-2X/6-31G(d) level of theory have been used to computationally design and test a pH-switchable electrostatic organocatalyst for Diels–Alder reactions. The successful catalyst design, bis(3-(3-phenylureido)benzyl)ammonium, was studied for the reaction of p-quinone with range of cyclic, heterocyclic, and acyclc dienes and also the reaction of cyclopentadiene with maleimide and N-phenylmaleimide. All reactions showed...[Show more]

CollectionsANU Research Publications
Date published: 2019
Type: Journal article
Source: Journal of Organic Chemistry
DOI: 10.1021/acs.joc.8b02940


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