Efficient O-Functionalization of Carbohydrates with Electrophilic Reagents

Research output: Contribution to journalArticle

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.

Details

Authors
  • Gergely L. Tolnai
  • Ulf J. Nilsson
  • Berit Olofsson
Organisations
External organisations
  • Stockholm University
Research areas and keywords

Subject classification (UKÄ) – MANDATORY

  • Organic Chemistry

Keywords

  • arylation, carbohydrates, electrophilic addition, fluorine, hypervalent compounds
Original languageEnglish
Pages (from-to)11226-11230
Number of pages5
JournalAngewandte Chemie (International edition)
Volume55
Issue number37
Publication statusPublished - 2016 Sep 1
Publication categoryResearch
Peer-reviewedYes