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Targeted Fluorination with the Fluoride Ion by Manganese‐Catalyzed Decarboxylation
Author(s) -
Huang Xiongyi,
Liu Wei,
Hooker Jacob M.,
Groves John T.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201500399
Subject(s) - decarboxylation , fluoride , chemistry , manganese , nucleophile , catalysis , carboxylic acid , fluorine , halogenation , ion , inorganic chemistry , organic chemistry , combinatorial chemistry
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 18 F labeling of a variety of carboxylic acids with radiochemical conversions up to 50 %, representing a targeted decarboxylative 18 F labeling method with no‐carrier‐added [ 18 F]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.