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 Нау. 2022
Accepted
14 Шіл. 2022
First published
15 Шіл. 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements