The non-heme iron halogenases, such as SyrB2 can chlorinate unactivated C-H bonds via a cis-oxochloroferrate(IV) intermediate in a “cis-rebound” strategy. While SyrB2 can also transfer bromide and azide, fluorine transfer using this oxidative strategy was not previously reported. Recently, our group has reported the cytochrome P450-inspired oxidative C-H fluorination using manganese porphyrin and manganese salen catalyst. We envisaged that this <i>cis-</i>coordination motif could be a useful mediator for C-H fluorination because the hydrogen abstraction and subsequent fluorine rebound process could occur within a solvent cage without the need for freely-diffusing substrate carbon radicals. We herein report the development of a new C-H fluorination using a non-heme manganese catalyst. In additions, this catalyst could enable the incorporation of [18F]fluoride into C-H bonds with high efficiency. A variety of building blocks and complex bioactive molecules is shown with radio-chemical conversions (RCCs) up to 72%. The conditions applied in this transformation empowers its future applications in PET imaging.

C-H fluorination mediated by a non-heme manganese complex

254th National Meeting (2017)

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