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02월 28일 17시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능
제123회 대한화학회 학술발표회, 총회 및 기기전시회 안내
Facile aromatic CF
substitution and [
labelingfrom aryl iodides by using the Cu ligand complex [(TMPhen)
2019년 2월 14일 15시 27분 10초
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4월 18일 (목요일) 11:00~12:30
Ji Young Choi
, Shyamsundar Das
, Dae Young Bae
, Eunsung Lee
, Byung Chul Lee
Transdisciplinary Studies, Seoul National University, Korea
Seoul National University Hospital, Korea
Department of Chemistry, Pohang University of Science and Technology, Korea
Department of Nuclear Medicine, Seoul National University Bundang Hospital, Korea
Drugs containing trifluoromethyl group have more high lipophilicity, in vivo stability and cell permeability. For this reason, aromatic trifluoromethylation and [
F]trifluoromethylation is very useful for development of new drugs as well as PET imaging agents. In this study, we explored the various ligands to discover the efficient ligand for copper mediated trifluoromethylation of aryl iodide. To figure out the most efficient ligand, a series of σ-donor and π-donor ligands were tested and compared the reactivity for trifluoromethylation. The CF
substitution was performed in presence of copper iodide, methylchlorodifluoroacetate (MCDFA), potassium fluoride, ligands and 1-iodo-4-nitrobenzene as a model compound. Based on condition of the CF
F]trifluoromethylation was carried out. As results, the most efficient ligand was 3,4,7,8-tetramehtylphenanthroline (TMPhen) that has the highest yields for trifluoromethylation (35.5 ± 8.4%,
≥ 3) as well as [
substitution (72 ± 2.0%,
≥ 3) as compared with reported ligand TMEDA (4.7 ± 0.7% and 44 ± 5.8%,
≥ 3, respectively) . In addition, [
F]trifluoromethylation of various aryl iodides obationed the desired products in moderate yields. The Cu ligand complex [(TMPhen)
Cl] was synthesized and analyzed by single X-ray crystal and NMR. The trifluoromethylation of model compound with complex gave desired product in more high yields (85.0 ± 1.4%). In this study, we investigated various ligands for trifluoromethylation to find the most efficient ligand. According to results, TMPhen was shown to best yields for CF
substitution. This methodology applied for the synthesis of various [
F]trifluoromethyl substituted arene derivatives.  M. Huiban, M. Tredwell, S. Mizuta, Z. Wan, X. Zhang, T. L. Collier, V. Gouverneur, J. Passchier, Nat. Chem., 2013;5:941–944.
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