title: Efficient O-Functionalization of Carbohydrates with Electrophilic Reagents.
abstract: Novel methodology for O-functionalization of carbohydrate derivatives has been established using bench-stable and easily prepared iodonium(III) reagents. Both electron-withdrawing and electron-donating aryl groups were introduced under ambient conditions and without precautions to exclude air or moisture. Furthermore, the approach was extended both to full arylation of cyclodextrin, and to trifluoroethylation of carbohydrate derivatives. This is the first general approach to introduce traditionally non-electrophilic groups into any of the OH groups around the sugar backbone. The methodology will be useful both in synthetic organic chemistry and biochemistry, as important functional groups can be incorporated under simple and robust reaction conditions in a fast and efficient manner.
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691, Stockholm, Sweden.
authors.forename: Gergely L
authors.initials: GL
authors.lastname: Tolnai
authors.affiliation: Centre for Analysis and Synthesis, Department of Chemistry, Lund University, 22100, Lund, Sweden.
authors.forename: Ulf J
authors.initials: UJ
authors.lastname: Nilsson
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691, Stockholm, Sweden. berit.olofsson@su.se.
authors.forename: Berit
authors.identifier: 0000-0001-7975-4582
authors.initials: B
authors.lastname: Olofsson
keywords: arylation; carbohydrates; electrophilic addition; fluorine; hypervalent compounds