{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T02:51:00Z","timestamp":1790823060990,"version":"4.1.0"},"reference-count":62,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2017,12,15]],"date-time":"2017-12-15T00:00:00Z","timestamp":1513296000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["ZL 65\/1-1"],"award-info":[{"award-number":["ZL 65\/1-1"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>In a recent contribution of Scott et al., the substrate scope of Cu-mediated nucleophilic radiofluorination with [18F]KF for the preparation of 18F-labeled arenes was extended to aryl- and vinylstannanes. Based on these findings, the potential of this reaction for the production of clinically relevant positron emission tomography (PET) tracers was investigated. To this end, Cu-mediated radiofluorodestannylation using trimethyl(phenyl)tin as a model substrate was re-evaluated with respect to different reaction parameters. The resulting labeling protocol was applied for 18F-fluorination of different electron-rich, -neutral and -poor arylstannyl substrates in RCCs of 16\u201388%. Furthermore, this method was utilized for the synthesis of 18F-labeled aromatic amino acids from additionally N-Boc protected commercially available stannyl precursors routinely applied for electrophilic radiohalogenation. Finally, an automated synthesis of 6-[18F]fluoro-l-m-tyrosine (6-[18F]FMT), 2-[18F]fluoro-l-tyrosine (2-[18F]F-Tyr), 6-[18F]fluoro-l-3,4-dihydroxyphenylalanine (6-[18F]FDOPA) and 3-O-methyl-6-[18F]FDOPA ([18F]OMFD) was established furnishing these PET probes in isolated radiochemical yields (RCYs) of 32\u201354% on a preparative scale. Remarkably, the automated radiosynthesis of 6-[18F]FDOPA afforded an exceptionally high RCY of 54 \u00b1 5% (n = 5).<\/jats:p>","DOI":"10.3390\/molecules22122231","type":"journal-article","created":{"date-parts":[[2017,12,15]],"date-time":"2017-12-15T12:23:56Z","timestamp":1513340636000},"page":"2231","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":39,"title":["A Practical Method for the Preparation of 18F-Labeled Aromatic Amino Acids from Nucleophilic [18F]Fluoride and Stannyl Precursors for Electrophilic Radiohalogenation"],"prefix":"10.3390","volume":"22","author":[{"given":"Fadi","family":"Zarrad","sequence":"first","affiliation":[{"name":"Institute of Neuroscience and Medicine, Nuclear Chemistry (INM-5), Forschungszentrum J\u00fclich GmbH, 52428 J\u00fclich, Germany"},{"name":"Institute of Radiochemistry and Experimental Molecular Imaging, University Clinic Cologne, 50931 Cologne, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5818-1260","authenticated-orcid":false,"given":"Boris","family":"Zlatopolskiy","sequence":"additional","affiliation":[{"name":"Institute of Neuroscience and Medicine, Nuclear Chemistry (INM-5), Forschungszentrum J\u00fclich GmbH, 52428 J\u00fclich, Germany"},{"name":"Institute of Radiochemistry and Experimental Molecular Imaging, University Clinic Cologne, 50931 Cologne, Germany"},{"name":"Max Planck Institute for Metabolism Research, Cologne 50931, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Philipp","family":"Krapf","sequence":"additional","affiliation":[{"name":"Institute of Neuroscience and Medicine, Nuclear Chemistry (INM-5), Forschungszentrum J\u00fclich GmbH, 52428 J\u00fclich, Germany"},{"name":"Institute of Radiochemistry and Experimental Molecular Imaging, University Clinic Cologne, 50931 Cologne, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3996-7473","authenticated-orcid":false,"given":"Johannes","family":"Zischler","sequence":"additional","affiliation":[{"name":"Institute of Neuroscience and Medicine, Nuclear Chemistry (INM-5), Forschungszentrum J\u00fclich GmbH, 52428 J\u00fclich, Germany"},{"name":"Institute of Radiochemistry and Experimental Molecular Imaging, University Clinic Cologne, 50931 Cologne, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5425-3116","authenticated-orcid":false,"given":"Bernd","family":"Neumaier","sequence":"additional","affiliation":[{"name":"Institute of Neuroscience and Medicine, Nuclear Chemistry (INM-5), Forschungszentrum J\u00fclich GmbH, 52428 J\u00fclich, Germany"},{"name":"Institute of Radiochemistry and Experimental Molecular Imaging, University Clinic Cologne, 50931 Cologne, Germany"},{"name":"Max Planck Institute for Metabolism Research, Cologne 50931, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2017,12,15]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"639","DOI":"10.1126\/science.1212625","article-title":"A fluoride-derived electrophilic late-stage fluorination reagent for PET imaging","volume":"334","author":"Lee","year":"2011","journal-title":"Science"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"450","DOI":"10.1002\/jlcr.2973","article-title":"Carrier-effect on palladium-catalyzed, nucleophilic 18F-fluorination of aryl triflates","volume":"55","author":"Cardinale","year":"2012","journal-title":"J. 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