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Efficient O-Functionalization of Carbohydrates with Electrophilic Reagents
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2016 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, no 37, 11226-11230 p.Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2016. Vol. 55, no 37, 11226-11230 p.
Keyword [en]
arylation, carbohydrates, electrophilic addition, fluorine, hypervalent compounds
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-135022DOI: 10.1002/anie.201605999ISI: 000383642300049PubMedID: 27528184OAI: oai:DiVA.org:su-135022DiVA: diva2:1045772
Conference
6th EuCheMS Chemistry Congress, Seville, Spain, Sep 11-15, 2016
Funder
Stiftelsen Olle Engkvist Byggmästare
Available from: 2016-11-10 Created: 2016-10-31 Last updated: 2017-06-13Bibliographically approved

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