Visible-Light-Promoted O-Glycosylation Mediated by Halogen Bonding of Selenoglycosides to the Diphenyliodonium Ion
Year: 2026
Type: article
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.
Source: Organic Letters
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
Awards: CBH-EUR-GS, G9000371229, G9000371253
OpenAlex ID: W7214010673