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Updated: Sep 3, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Photoacid-catalyzed acetalization of carbonyls with alcohols
Jason Saway1, Abigail F Pierre1, Joseph J Badillo1
1Department of Chemistry and Biochemistry, Seton Hall University, 400 South Orange Avenue, South Orange, NJ, 07079, USA. joseph.badillo@shu.edu.
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.
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