Site-selective 18F Fluorination Of Unactivated C–H Bonds Mediated ...

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

Wei Liu,a Xiongyi Huang,a Michael S. Placzek,bc Shane W. Krska,d Paul McQuade,e Jacob M. Hooker*bc and John T. Groves *a Author affiliations

* Corresponding authors

a Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA E-mail: [email protected]

b Athinoula A. Martinos Center for Biomedical Imaging, Massachusetts General Hospital, Harvard Medical School, Charlestown, Massachusetts 02129, USA E-mail: [email protected]

c Division of Nuclear Medicine and Molecular Imaging, Department of Radiology, Massachusetts General Hospital, Boston, Massachusetts 02114, USA

d Department of Process Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, USA

e 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.

This article is Open Access Please wait while we load your content... Something went wrong. Try again?