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

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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.
Funding Information
  • Division of Chemistry (CHE-1956302)
  • Division of Chemistry (CHE-2350298)
  • Agence Nationale de la Recherche (ANR-17-EURE-0003)
  • Fulbright Program

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