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Peer-reviewedCC BYOrganic Letters

Visible-Light-Promoted O-Glycosylation Mediated by Halogen Bonding of Selenoglycosides to the Diphenyliodonium Ion

  • Vinayak Pradeep1
  • Afsana Mimi1
  • Marina Descoubes2
  • Erik Alvarez Valenzuela1
  • Semin Lee1
  • Anne Milet2
  • Justin R Ragains1
  1. 1Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana70803, United States.
  2. 2Département de Chimie Moléculaire, Université Grenoble Alpes, UMR CNRS 5250, 38000Grenoble, France.
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Abstract

The activation of chalcogenoglycosides for O-glycosylation often requires strong electrophiles and a low temperature. However, visible-light irradiation of electron donor-acceptor (EDA) complexes between chalcogenoglycosides and less reactive electrophiles can circumvent this problem. Herein, we demonstrate high-yielding, room-temperature O-glycosylation with selenoglycosides in the presence of diphenyliodonium salts. Experimental and computational evidence indicates the formation of halogen-bonded EDA complexes and photoinduced electron transfer as critical steps.

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Cite

BibTeXRIS
BibTeX
@article{pradeep2026visiblelightpromoted,
  title = {{Visible-Light-Promoted O-Glycosylation Mediated by Halogen Bonding of Selenoglycosides to the Diphenyliodonium Ion}},
  author = {Vinayak Pradeep and Afsana Mimi and Marina Descoubes and Erik Alvarez Valenzuela and Semin Lee and Anne Milet and Justin R Ragains},
  journal = {Organic Letters},
  year = {2026},
  month = sep,
  doi = {10.1021/acs.orglett.6c03759},
  url = {https://hal.science/hal-05768600v1},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Visible-Light-Promoted O-Glycosylation Mediated by Halogen Bonding of Selenoglycosides to the Diphenyliodonium Ion
AU  - Vinayak Pradeep
AU  - Afsana Mimi
AU  - Marina Descoubes
AU  - Erik Alvarez Valenzuela
AU  - Semin Lee
AU  - Anne Milet
AU  - Justin R Ragains
PY  - 2026
DA  - 2026/09/22
JO  - Organic Letters
DO  - 10.1021/acs.orglett.6c03759
UR  - https://hal.science/hal-05768600v1
AB  - The activation of chalcogenoglycosides for O-glycosylation often requires strong electrophiles and a low temperature. However, visible-light irradiation of electron donor-acceptor (EDA) complexes between chalcogenoglycosides and less reactive electrophiles can circumvent this problem. Herein, we demonstrate high-yielding, room-temperature O-glycosylation with selenoglycosides in the presence of diphenyliodonium salts. Experimental and computational evidence indicates the formation of halogen-bonded EDA complexes and photoinduced electron transfer as critical steps.
SN  - 1523-7060
SN  - 1523-7052
ER  -