Journal article
Direct Trifluoromethylation of Alcohols Using a Hypervalent Iodosulfoximine Reagent.
- Togni A ETH Zurich, Department of Chemistry, Vladimir-Prelog-Weg 2, CH-8093, Zurich, SWITZERLAND.
- Kalim J ETH Zurich, Department of Chemistry, SWITZERLAND.
- Pietrasiak E Pahong University, Chemistry, KOREA, REPUBLIC OF.
- Duhail T Universite Paris-Saclay, Institut Lavoisier, FRANCE.
- Anselmi E Université de Tours, Faculté des Sciences, FRANCE.
- Magnier E Universite Paris-Saclay, Institut Lavoisier, FRANCE.
- 2020-11-26
Published in:
- Chemistry (Weinheim an der Bergstrasse, Germany). - 2020
English
The direct trifluoromethylation of a variety of aliphatic alcohols using a hypervalent iodosulfoximine reagent affords the corresponding ethers in moderate to good yields (14-72%). Primary, secondary and even tertiary alcohols, including examples derived from natural products, undergo this transformation in the presence of catalytic amounts of zinc bis(triflimide). Typical reaction conditions involve a neat mixture of 6.0 equivalents of the alcohol with 1.0 equivalent of the reagent, with the majority of reactions complete within 2 h with 2.5 mol-% of the Lewis acid catalyst. Furthermore, we provide experimental evidence that the C-O bond-forming process occurs via the coordination of the alcohol to the iodine atom and subsequent reductive elimination.
- Language
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- English
- Open access status
- closed
- Identifiers
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- DOI 10.1002/chem.202005104
- PMID 33241882
- Persistent URL
- https://folia.unifr.ch/global/documents/76196
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