Photoacid-catalyzed acetalization of carbonyls with alcohols

Org Biomol Chem. 2022 Aug 10;20(31):6188-6192. doi: 10.1039/d2ob00435f.

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acetals*
  • Alcohols*
  • Aldehydes
  • Catalysis
  • Molecular Structure

Substances

  • Acetals
  • Alcohols
  • Aldehydes