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- Title
Targeted Fluorination with the Fluoride Ion by Manganese-Catalyzed Decarboxylation.
- Authors
Huang, Xiongyi; Liu, Wei; Hooker, Jacob M.; Groves, John T.
- Abstract
We describe the first catalytic decarboxylative fluorination reaction based on the nucleophilic fluoride ion. The reported method allows the facile replacement of various aliphatic carboxylic acid groups with fluorine. Moreover, the potential of this method for PET imaging has been demonstrated by the successful 18F labeling of a variety of carboxylic acids with radiochemical conversions up to 50 %, representing a targeted decarboxylative 18F labeling method with no-carrier-added [18F]fluoride. Mechanistic probes suggest that the reaction proceeds through the interaction of the manganese catalyst with iodine(III) carboxylates formed in situ from iodosylbenzene and the carboxylic acid substrates.
- Subjects
FLUORINATION; CARBOXYLIC acids; DECARBOXYLATION; RADIOCHEMICAL separation; ORGANOFLUORINE compounds
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 17, p5330
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201500399