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Title: Site-selective 18 F fluorination of unactivated C–H bonds mediated by a manganese porphyrin

Abstract

A direct aliphatic C–H 18 F labeling method using [ 18 F]fluoride ion at inaccessible and unreactive sites is reported.

Authors:
 [1];  [1];  [2];  [3];  [4];  [2]; ORCiD logo [1]
  1. Department of Chemistry, Princeton University, USA
  2. Athinoula A. Martinos Center for Biomedical Imaging, Massachusetts General Hospital, Harvard Medical School, USA, Division of Nuclear Medicine and Molecular Imaging
  3. Department of Process Chemistry, Merck Research Laboratories, Rahway, USA
  4. Imaging Research, Merck Research Laboratories, USA
Publication Date:
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1413343
Grant/Contract Number:
DE SC0001298
Resource Type:
Journal Article: Published Article
Journal Name:
Chemical Science
Additional Journal Information:
Journal Volume: 9; Journal Issue: 5; Related Information: CHORUS Timestamp: 2018-01-31 08:52:57; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

Liu, Wei, Huang, Xiongyi, Placzek, Michael S., Krska, Shane W., McQuade, Paul, Hooker, Jacob M., and Groves, John T.. Site-selective 18 F fluorination of unactivated C–H bonds mediated by a manganese porphyrin. United Kingdom: N. p., 2018. Web. doi:10.1039/C7SC04545J.
Liu, Wei, Huang, Xiongyi, Placzek, Michael S., Krska, Shane W., McQuade, Paul, Hooker, Jacob M., & Groves, John T.. Site-selective 18 F fluorination of unactivated C–H bonds mediated by a manganese porphyrin. United Kingdom. doi:10.1039/C7SC04545J.
Liu, Wei, Huang, Xiongyi, Placzek, Michael S., Krska, Shane W., McQuade, Paul, Hooker, Jacob M., and Groves, John T.. Mon . "Site-selective 18 F fluorination of unactivated C–H bonds mediated by a manganese porphyrin". United Kingdom. doi:10.1039/C7SC04545J.
@article{osti_1413343,
title = {Site-selective 18 F fluorination of unactivated C–H bonds mediated by a manganese porphyrin},
author = {Liu, Wei and Huang, Xiongyi and Placzek, Michael S. and Krska, Shane W. and McQuade, Paul and Hooker, Jacob M. and Groves, John T.},
abstractNote = {A direct aliphatic C–H 18 F labeling method using [ 18 F]fluoride ion at inaccessible and unreactive sites is reported.},
doi = {10.1039/C7SC04545J},
journal = {Chemical Science},
number = 5,
volume = 9,
place = {United Kingdom},
year = {Mon Jan 01 00:00:00 EST 2018},
month = {Mon Jan 01 00:00:00 EST 2018}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record at 10.1039/C7SC04545J

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  • This communication describes a method for the nucleophilic radiofluorination of electron-rich arenes. The reaction involves the initial C(sp 2)–H functionalization of an electron-rich arene with MesI(OH)OTs to form a (mesityl)(aryl)iodonium salt. This salt is then used in situ in a Cu-mediated radiofluorination with [ 18F]KF. This approach leverages the stability and availability of electron-rich arene starting materials to enable mild late-stage radiofluorination of toluene, anisole, aniline, pyrrole, and thiophene derivatives. Finally, the radiofluorination has been automated to access a 41 mCi dose of an 18F-labeled nimesulide derivative in high (2800 ± 700 Ci/mmol) specific activity.
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  • This communication describes a method for the nucleophilic radiofluorination of electron-rich arenes. The reaction involves the initial C(sp 2)–H functionalization of an electron-rich arene with MesI(OH)OTs to form a (mesityl)(aryl)iodonium salt. This salt is then used in situ in a Cu-mediated radiofluorination with [ 18F]KF. This approach leverages the stability and availability of electron-rich arene starting materials to enable mild late-stage radiofluorination of toluene, anisole, aniline, pyrrole, and thiophene derivatives. Finally, the radiofluorination has been automated to access a 41 mCi dose of an 18F-labeled nimesulide derivative in high (2800 ± 700 Ci/mmol) specific activity.
  • Here, a copper-mediated radiofluorination of aryl- and vinylboronic acids with K 18F is described. This method exhibits high functional group tolerance and is effective for the radiofluorination of a range of electron-deficient, -neutral, and -rich aryl-, heteroaryl-, and vinylboronic acids. This method has been applied to the synthesis of [ 18F]FPEB, a PET radiotracer for quantifying metabotropic glutamate 5 receptors.
    Cited by 36
  • Here, a copper-mediated radiofluorination of aryl- and vinylboronic acids with K 18F is described. This method exhibits high functional group tolerance and is effective for the radiofluorination of a range of electron-deficient, -neutral, and -rich aryl-, heteroaryl-, and vinylboronic acids. This method has been applied to the synthesis of [ 18F]FPEB, a PET radiotracer for quantifying metabotropic glutamate 5 receptors.