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.

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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
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article

Purple Light-Promoted Ferrier Photobromination of O -Benzoylated Carbohydrates in Benzotrifluoride

Scott A. Cameron, Nicholas W. See, Norbert Wimmer, Vito Ferro et al.
The Journal of Organic Chemistry
Carbohydrate Chemistry and Synthesis
article

Purple Light-Promoted Ferrier Photobromination of O -Benzoylated Carbohydrates in Benzotrifluoride

Scott A. Cameron, Nicholas W. See, Norbert Wimmer, Vito Ferro, Richard H. Furneaux, Ajay Sharma S, Michael J. Godinez, Guoqing Zhang
article en

Abstract

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.

The Journal of Organic ChemistryVol. 90(47)
The University of Queensland (AU), Victoria University of Wellington (NZ)
Openalex Percentile: Top 74%
Carbohydrate Chemistry and Synthesis
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