Hole Catalysis of Cycloaddition Reactions: How to Activate and Control Oxidant Upconversion in Radical-Cationic Diels–Alder Reactions

• Published in: Journal of the American Chemical Society Vol. 145; no. 35; pp. 19354 - 19367
• Main Authors: Chabuka, Beauty K., Alabugin, Igor V.
• Format: Journal Article
• Language: English
• Published: American Chemical Society 06.09.2023
• Subjects: catalysts; catalytic activity; cations; cycloaddition reactions; oxidants; oxidation; thermodynamics

In order to use holes as catalysts, the oxidized product should be able to transfer the hole to a fresh reactant. For that, the hole-catalyzed reaction must increase the oxidation potential along the reaction path, i.e., lead to “hole upconversion.” If this thermodynamic requirement is satisfied, a...