Issue 31, 2022

Photoacid-catalyzed acetalization of carbonyls with alcohols

Abstract

In this report, we demonstrate that visible light photoactivation of 6-bromo-2-naphthol facilitates the photoacid-catalyzed acetalization of carbonyls with alcohols. We also demonstrate that 2-naphthol when coupled to a photosensitizer provides acetals from electron-deficient aldehydes. In addition, the S1 excited state pKa for 6-bromo-2-naphthol in water was determined and shown to have increased excited-state acidity relative to 2-naphthol.

Graphical abstract: Photoacid-catalyzed acetalization of carbonyls with alcohols

  • This article is part of the themed collection: New Talent

Supplementary files

Article information

Article type
Communication
Submitted
03 Mär 2022
Accepted
14 Jul 2022
First published
15 Jul 2022

Org. Biomol. Chem., 2022,20, 6188-6192

Author version available

Photoacid-catalyzed acetalization of carbonyls with alcohols

J. Saway, A. F. Pierre and J. J. Badillo, Org. Biomol. Chem., 2022, 20, 6188 DOI: 10.1039/D2OB00435F

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