18 F labeling strategies for unmodified peptides with [ 18 F]fluoride require 18 F-labeled prosthetics for bioconjugation more often with cysteine thiols or lysine amines. Here we explore selective radical chemistry to target aromatic residues applying C− H 18 F-trifluoromethylation. We report a one-step route to [ 18 F]CF 3 SO 2 NH 4 from [ 18 F]fluoride and its application to direct [ 18 F]CF 3 incorporation at tryptophan or tyrosine residues using unmodified peptides as complex as recombinant human insulin. The fully automated radiosynthesis of octreotide[Trp(2-CF 2 18 F)] enables in vivo positron emission tomography imaging.Communication pubs.acs.org/JACS

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The poly­(ADP-ribose) polymerase (PARP) inhibitor rucaparib is used in the clinic to treat BRCA-mutated cancers. Herein, we report two strategies to access the 18F-isotopologue of rucaparib by applying a copper-mediated nucleophilic 18F-fluorodeboronation. The most successful approach features an aldehydic boronic ester precursor that is subjected to reductive amination post-18F-labeling and affords [18F]­rucaparib with an activity yield of 11% ± 3% (n = 3) and a molar activity (A m) up to 30 GBq/μmol. Preliminary in vitro studies are presented.