title: Oxidative cyclizations, the synthesis of aryl-substituted C-glycosides, and the role of the second electron transfer step.
abstract: Anodic oxidation reactions have been used to synthesize aryl- and biaryl-substituted C-glycosides. The reactions take advantage of the tendency for alcohol nucleophiles to trap nonpolar radical cations. The addition of the alcohol to the radical cation appears to be reversible, and the success of the cyclizations is dependent on the ease with which the resulting benzylic radical is oxidized.
authors.affiliation: Department of Chemistry, Washington University in St. Louis , St. Louis, Missouri 63130, United States.
authors.forename: Jake A
authors.initials: JA
authors.lastname: Smith
authors.forename: Kevin D
authors.initials: KD
authors.lastname: Moeller
mesh_terms: D002412:Cations / Q000737:chemistry; D004579:Electron Transport; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D002412:Cations; D006027:Glycosides