title: A Visible-Light-Promoted O-Glycosylation with a Thioglycoside Donor.
abstract: Visible-light irradiation of 4-p-methoxyphenyl-3-butenylthioglucoside donors in the presence of Umemoto's reagent and alcohol acceptors serves as a mild approach to O-glycosylation. Visible-light photocatalysts are not required for activation, and alkyl- and arylthioglycosides not bearing the p-methoxystyrene are inert to these conditions. Experimental and computational evidence for an intervening electron donor-acceptor complex, which is necessary for reactivity, is provided. Yields with primary, secondary, and tertiary alcohol acceptors range from moderate to high. Complete β-selectivity can be attained through neighboring-group participation.
authors.affiliation: Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803, USA.
authors.forename: Mark L
authors.initials: ML
authors.lastname: Spell
authors.affiliation: Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803, USA.
authors.forename: Kristina
authors.initials: K
authors.lastname: Deveaux
authors.affiliation: Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803, USA.
authors.forename: Caitlin G
authors.initials: CG
authors.lastname: Bresnahan
authors.affiliation: Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803, USA.
authors.forename: Bradley L
authors.initials: BL
authors.lastname: Bernard
authors.affiliation: Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803, USA.
authors.forename: William
authors.initials: W
authors.lastname: Sheffield
authors.affiliation: Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803, USA.
authors.forename: Revati
authors.initials: R
authors.lastname: Kumar
authors.affiliation: Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803, USA. jragains@lsu.edu.
authors.forename: Justin R
authors.identifier: 0000-0002-2521-5396
authors.initials: JR
authors.lastname: Ragains
keywords: glycosylation; photochemistry; reaction mechanisms; sulfur