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Alcohol‐Enhanced Cu‐Mediated Radiofluorination
Author(s) -
Zischler Johannes,
Kolks Niklas,
Modemann Daniel,
Neumaier Bernd,
Zlatopolskiy Boris D.
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604633
Subject(s) - radiosynthesis , chemistry , combinatorial chemistry , alcohol , phenols , pet imaging , organic chemistry , positron emission tomography , nuclear medicine , medicine
The potential of many 18 F‐labeled (hetero)aromatics for applications in positron emission tomography remains underexplored because convenient procedures for their radiosynthesis are lacking. Consequently, simple methods to prepare radiofluorinated (hetero)arenes are highly sought after. Herein, we report the beneficial effect of primary and secondary alcohols on Cu‐mediated 18 F‐labeling. This observation contradicts the assumption that such alcohols are inappropriate solvents for aromatic fluorination. Therefore, we developed a protocol for rapid radiolabeling of an extraordinarily broad scope of boronic and stannyl substrates under general reaction conditions. Notably, radiofluorinated indoles, phenols, and anilines were synthesized directly from the corresponding unprotected precursors. Furthermore, the novel method enabled the preparation of radiofluorinated tryptophans, [ 18 F]F‐DPA, [ 18 F]DAA1106, 6‐[ 18 F]FDA, and 6‐[ 18 F]FDOPA.