期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 17, 页码 5241-5245出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201500399
关键词
decarboxylation; fluoride; fluorination; labeling with F-18; manganese porphyrins
资金
- US National Science Foundation [CHE-1148597]
- Center for Catalytic Hydrocarbon Functionalization, an Energy Frontier Research Center, U.S. Department of Energy, Office of Science, Basic Energy Sciences [DE SC0001298]
- Center for Functional Neuroimaging Technologies [P41EB015896, S10RR017208, S10RR023452]
- Howard Hughes Medical Institute
- Merck, Inc.
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1148597] Funding Source: National Science Foundation
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 F-18 labeling of a variety of carboxylic acids with radiochemical conversions up to 50%, representing a targeted decarboxylative F-18 labeling method with no-carrier-added [F-18] 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.
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