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Title: Targeted Fluorination with the Fluoride Ion by Manganese-Catalyzed Decarboxylation

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.

Authors:
; ; ;
Publication Date:
Research Org.:
Energy Frontier Research Centers (EFRC) (United States). Center for Catalytic Hydrocarbon Functionalization (CCHF)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1385893
DOE Contract Number:  
SC0001298
Resource Type:
Journal Article
Resource Relation:
Journal Name: Angewandte Chemie (International Edition); Journal Volume: 54; Journal Issue: 17; Related Information: CCHF partners with University of Virginia (lead); Brigham Young University; California Institute of Technology; Colorado School of Mines; University of Maryland; University of North Carolina, Chapel Hill; University of North Texas; Princeton University; The Scripps Research Institute; Yale University
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; catalysis (homogeneous), catalysis (heterogeneous), bio-inspired, hydrogen and fuel cells, materials and chemistry by design, synthesis (novel materials)

Citation Formats

Huang, Xiongyi, Liu, Wei, Hooker, Jacob M., and Groves, John T. Targeted Fluorination with the Fluoride Ion by Manganese-Catalyzed Decarboxylation. United States: N. p., 2015. Web. doi:10.1002/anie.201500399.
Huang, Xiongyi, Liu, Wei, Hooker, Jacob M., & Groves, John T. Targeted Fluorination with the Fluoride Ion by Manganese-Catalyzed Decarboxylation. United States. doi:10.1002/anie.201500399.
Huang, Xiongyi, Liu, Wei, Hooker, Jacob M., and Groves, John T. Tue . "Targeted Fluorination with the Fluoride Ion by Manganese-Catalyzed Decarboxylation". United States. doi:10.1002/anie.201500399.
@article{osti_1385893,
title = {Targeted Fluorination with the Fluoride Ion by Manganese-Catalyzed Decarboxylation},
author = {Huang, Xiongyi and Liu, Wei and Hooker, Jacob M. and Groves, John T.},
abstractNote = {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.},
doi = {10.1002/anie.201500399},
journal = {Angewandte Chemie (International Edition)},
number = 17,
volume = 54,
place = {United States},
year = {Tue Mar 03 00:00:00 EST 2015},
month = {Tue Mar 03 00:00:00 EST 2015}
}