期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 25, 页码 6473-6476出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201402238
关键词
carbenes; copper; fluorine; isotopic labeling; phase-transfer catalysis
资金
- Royalty Research Fund at University of Washington
- NSF (CAREER) [1254636]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1254636] Funding Source: National Science Foundation
A chemoselective catalytic fluorination of alkyl triflates is described using potassium fluoride as a fluoride source. Excellent yields of the desired alkyl fluorides are obtained after one hour at 45 degrees C using 2 mol% of the copper catalyst. With 10 mol% of the catalyst, full conversion can be achieved in less than 10 minutes at 45 degrees C, and thus makes this procedure potentially suited for the preparation of 18F-labeled PET probes. As a result of the mild reaction conditions, only the substitution products are observed with no evidence of common side reactions, such as elimination. Reported is a preliminary study of the reaction scope, which demonstrates that the fluorination can be performed in the presence of a wide range of functional groups. Evidence suggests an unusual role of the [IPrCuOTf] catalyst as a phase-transfer catalyst and points to [IPrCuF] as the active fluorinating reagent (IPr= 1,3-bis( 2,6-diisopropylphenyl) imidazol-2-ylidene).
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