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제123회 대한화학회 학술발표회, 총회 및 기기전시회 안내
BTC5A (Bis-Triethylene glycol-functionalized Crown-5-calixArene) analogs as a new phase-transfer catalysts for nucleophilic aromatic [
2019년 2월 14일 15시 36분 22초
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4월 18일 (목요일) 11:00~12:30
, Byung Chul Lee
, Dong Wook Kim
Department of Transdisciplinary Studies, Graduate School of Convergence Science and Technology, Korea
Department of Nuclear Medicine, Seoul National University Bundang Hospital, Korea
Department of Chemistry, Inha University, Korea
Aromatic fluorine-18 labeling into the bioactive molecule is essential for in vivo stability and retaining its biological activities as PET radiotracers. As the above reason, new effective incorporation of fluorine-18 into arene is always in demand. Herein, we intend to achieve an effective aromatic [
F]fluorination in various conditions by using BTC5A analogs as a new phase transfer catalyst. We evaluated the reactivity of six differently substituted biphenyl precursors and chosen diaryliodonium salt precursors as the desirable precursor. In the stability test of precursors with PTC in basic conditions showed up to 30% higher stability in case of BTC5A analogs compare to Kryptofix2.2.2 (K
). When using TEMPO as radical scavenger with PTC, showed that precursor was more stable in basic conditions. After the stability test, aromatic fluorination from the precursor by using KF with BTC5A analogs were performed in the optimized condition and showed that highest yields up to 80% which is about 10 times higher than K
. In fluorine-18 labeling experiments, the radiochemical yield (RCY) in the presence of BTC5A analogs & TEMPO showed up to 82% which is three times higher than that in the presence of using K
. We also found that RCY was about 40% even though only 10 mole% of BTC5A analogs was used. In this study, we could successfully optimize the condition for the F-18 labeling by using BTC5A analogs which is more effective than K
. We are expecting that BTC5A analogs as an organic promoter could be an alternative catalyst for aromatic [
F]fluorination and also help to develop new radiopharmaceuticals.  Dong Wook Kim, et al. Chem. Eur. J. 2016, 22, 4515-1520  Byung Chul Lee, et al. Org. Biomol. Chem. 2011, 9 , 8346-8355
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