title: An air- and water-stable iodonium salt promoter for facile thioglycoside activation.
abstract: The air- and water-stable iodonium salt phenyl(trifluoroethyl)iodonium triflimide is shown to activate thioglycosides for glycosylation at room temperature. Both armed and disarmed thioglycosides rapidly undergo glycosylation in 68-97% yield. The reaction conditions are mild and do not require strict exclusion of air and moisture. The operational simplicity of the method should allow experimentalists with a limited synthetic background to construct glycosidic linkages.
authors.affiliation: Department of Chemistry, Tufts University , 62 Talbot Avenue, Medford, Massachusetts 02155, United States.
authors.forename: An-Hsiang Adam
authors.initials: AH
authors.lastname: Chu
authors.forename: Andrei
authors.initials: A
authors.lastname: Minciunescu
authors.forename: Vittorio
authors.initials: V
authors.lastname: Montanari
authors.forename: Krishna
authors.initials: K
authors.lastname: Kumar
authors.forename: Clay S
authors.initials: CS
authors.lastname: Bennett
mesh_terms: D000388:Air; D005740:Gases; D006031:Glycosylation; D008698:Mesylates; D015394:Molecular Structure; D013237:Stereoisomerism; D013865:Thioglycosides / Q000737:chemistry*; D014867:Water
chemical_list: D005740:Gases; D008698:Mesylates; D013865:Thioglycosides; D014867:Water