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Efficient O-Functionalization of Carbohydrates with Electrophilic Reagents

Tolnai, Gergely L.; Nilsson, Ulf J. LU and Olofsson, Berit (2016) In Angewandte Chemie (International edition) 55(37). p.11226-11230
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... (More)

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.

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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
arylation, carbohydrates, electrophilic addition, fluorine, hypervalent compounds
in
Angewandte Chemie (International edition)
volume
55
issue
37
pages
5 pages
publisher
John Wiley & Sons
external identifiers
  • scopus:84990198892
  • wos:000383642300049
ISSN
1433-7851
DOI
10.1002/anie.201605999
language
English
LU publication?
yes
id
89e40dab-2b05-46f0-8155-2ea2a84eaac9
date added to LUP
2016-11-23 12:22:01
date last changed
2017-11-19 04:35:04
@article{89e40dab-2b05-46f0-8155-2ea2a84eaac9,
  abstract     = {<p>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.</p>},
  author       = {Tolnai, Gergely L. and Nilsson, Ulf J. and Olofsson, Berit},
  issn         = {1433-7851},
  keyword      = {arylation,carbohydrates,electrophilic addition,fluorine,hypervalent compounds},
  language     = {eng},
  month        = {09},
  number       = {37},
  pages        = {11226--11230},
  publisher    = {John Wiley & Sons},
  series       = {Angewandte Chemie (International edition)},
  title        = {Efficient O-Functionalization of Carbohydrates with Electrophilic Reagents},
  url          = {http://dx.doi.org/10.1002/anie.201605999},
  volume       = {55},
  year         = {2016},
}