Targeted fluorination with the fluoride ion by manganese-catalyzed decarboxylation

Xiongyi Huang, Wei Liu, Jacob M. Hooker, John Taylor Groves

Research output: Contribution to journalArticle

74 Scopus citations

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. Nucleophile first: An efficient manganese porphyrin catalyzed decarboxylative fluorination reaction based on a nucleophilic fluorine source is described. The potential of the described method for use in PET imaging has been demonstrated by the successful 18F labeling of various aliphatic carboxylic acids, representing the first decarboxylative 18F labeling method with no-carrier-added [18F]fluoride.

Original languageEnglish (US)
Pages (from-to)5241-5245
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number17
DOIs
StatePublished - Apr 20 2015

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • decarboxylation
  • fluoride
  • fluorination
  • labeling with F
  • manganese porphyrins

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