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Efficient O‐Functionalization of Carbohydrates with Electrophilic Reagents
Author(s) -
Tolnai Gergely L.,
Nilsson Ulf J.,
Olofsson Berit
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201605999
Subject(s) - electrophile , surface modification , chemistry , reagent , aryl , carbohydrate , combinatorial chemistry , organic chemistry , carbohydrate chemistry , electrophilic addition , catalysis , alkyl
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.