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

Wei Liu; Xiongyi Huang; Michael S Placzek; Shane W Krska; Paul McQuade; Jacob M Hooker; John T Groves

doi:10.1039/c7sc04545j

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

Chem Sci. 2017 Dec 5;9(5):1168-1172. doi: 10.1039/c7sc04545j. eCollection 2018 Feb 7.

Authors

Wei Liu¹, Xiongyi Huang¹, Michael S Placzek^{2

3}, Shane W Krska⁴, Paul McQuade⁵, Jacob M Hooker^{2

3}, John T Groves¹

Affiliations

¹ Department of Chemistry , Princeton University , Princeton , New Jersey 08544 , USA . Email: jtgroves@princeton.edu.
² Athinoula A. Martinos Center for Biomedical Imaging , Massachusetts General Hospital , Harvard Medical School , Charlestown , Massachusetts 02129 , USA . Email: hooker@nmr.mgh.harvard.edu.
³ Division of Nuclear Medicine and Molecular Imaging , Department of Radiology , Massachusetts General Hospital , Boston , Massachusetts 02114 , USA.
⁴ Department of Process Chemistry , Merck Research Laboratories , Rahway , New Jersey 07065 , USA.
⁵ Imaging Research , Merck Research Laboratories , West Point , Pennsylvania 19486 , USA.

Abstract

The first direct C-H ¹⁸F fluorination reaction of unactivated aliphatic sites using no-carrier-added [¹⁸F]fluoride is reported. Under the influence of a manganese porphyrin/iodosylbenzene system, a variety of unactivated aliphatic C-H bonds can be selectively converted to C-¹⁸F bonds. The mild conditions, broad substrate scope and generally inaccessible regiochemistry make this radio-fluorination a powerful alternate to established nucleophilic substitution for the preparation of ¹⁸F labeled radio tracers.

Abstract

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