This presentation will discuss the development of a photoacid-catalyzed acetalization of aldehydes with alcohols. We demonstrate that 6-bromo-2-naphthol functions as a photoacid catalyst for the formation of a range of acetals and ketals. These acetal and ketal products often serve as protecting groups enabling the synthesis of complex natural products and pharmaceuticals. Studies conducted using NMR spectroscopy on a mixture of 6-bromo-2-naphthol and benzaldehyde show a broadening and a downfield shifting of the catalyst hydroxyl peak, suggesting enhanced hydrogen bonding is responsible for increased catalyst acidity after irradiation. The determination of photoacid catalyst ground-state and excited-state acidities will also be discussed.

Photoacid-catalyzed acetalization of carbonyl compounds

ACS Spring 2022

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