Efficient O-Functionalization of Carbohydrates with Electrophilic Reagents
(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
- Tolnai, Gergely L. ; Nilsson, Ulf J. LU and Olofsson, Berit
- organization
- publishing date
- 2016-09-01
- 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 Inc.
- external identifiers
-
- wos:000383642300049
- pmid:27528184
- scopus:84990198892
- 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
- 2024-05-04 13:32:48
@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}},
keywords = {{arylation; carbohydrates; electrophilic addition; fluorine; hypervalent compounds}},
language = {{eng}},
month = {{09}},
number = {{37}},
pages = {{11226--11230}},
publisher = {{John Wiley & Sons Inc.}},
series = {{Angewandte Chemie (International edition)}},
title = {{Efficient O-Functionalization of Carbohydrates with Electrophilic Reagents}},
url = {{http://dx.doi.org/10.1002/anie.201605999}},
doi = {{10.1002/anie.201605999}},
volume = {{55}},
year = {{2016}},
}