A Visible‐Light‐Driven <i>O</i> ‐Glycosylation with Selenoglycosides Mediated by Chalcogen Bonding to Umemoto's Reagent
The activation of chalcogenoglycosides for O-glycosylation typically involves strong electrophiles requiring low temperature. Herein, we demonstrate that visible-light irradiation of selenoglycosides in the presence of Umemoto's reagent results in often high-yielding O-glycosylation. We provide evidence that this process is mediated by a novel mode of reactivity, specifically photoinduced electron transfer within a chalcogen-bonded complex.
Authors
- Justin R. Ragains (ORCID: https://orcid.org/0000-0002-2521-5396)
- J. E. Y. Dobson (ORCID: https://orcid.org/0000-0002-4911-598X)
- Kenneth A. Lopata (ORCID: https://orcid.org/0000-0002-9141-684X)
- Xinhua He (ORCID: https://orcid.org/0000-0001-7826-2973)
- Erik Alvarez Valenzuela
- Semin Lee (ORCID: https://orcid.org/0000-0002-9015-6046)
- Tiffany Duong
- Vinayak Pradeep
Institutions
- Louisiana State University (US)
- Louisiana State University Agricultural Center (US)
- Nicholls State University (US)
Publication Details
- Journal
- Angewandte Chemie International Edition
- Published
- 2025-05-09
- DOI
- https://doi.org/10.1002/anie.202508424
- Citations
- 5
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 4.68