Purple Light-Promoted Ferrier Photobromination of <i>O</i> -Benzoylated Carbohydrates in Benzotrifluoride
Our laboratory has previously reported on a contemporary Ferrier photobromination which circumvents critical limitations of the original reaction. The new conditions provide highly efficient and scalable routes to <i>O</i>-acetylated 5-<i>C</i>-bromosugars but cannot be used to access <i>O</i>-benzoylated derivatives. Herein, we show that the scope of the Ferrier photobromination can be expanded to encompass important <i>O</i>-benzoylated carbohydrates by a simple but effective modification of the reaction conditions. This advance importantly paves the way for improved syntheses of glycosidase inhibitors and rare L-hexoses.
Authors
- Scott A. Cameron (ORCID: https://orcid.org/0000-0003-2669-8622)
- Nicholas W. See (ORCID: https://orcid.org/0000-0002-8038-634X)
- Norbert Wimmer (ORCID: https://orcid.org/0000-0002-7178-8101)
- Vito Ferro (ORCID: https://orcid.org/0000-0003-3306-2550)
- Richard H. Furneaux (ORCID: https://orcid.org/0000-0003-0973-2606)
- Ajay Sharma S (ORCID: https://orcid.org/0000-0001-7497-9694)
- Michael J. Godinez
- Guoqing Zhang (ORCID: https://orcid.org/0000-0002-1755-534X)
Institutions
- The University of Queensland (AU)
- Victoria University of Wellington (NZ)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-11-14
- DOI
- https://doi.org/10.1021/acs.joc.5c01913
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00