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제123회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Facile aromatic CF3 substitution and [18F]CF3 labelingfrom aryl iodides by using the Cu ligand complex [(TMPhen)2Cu][COOCF2Cl]

2019년 2월 14일 15시 27분 10초
ORGN.P-346 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
4월 18일 (목요일) 11:00~12:30
Organic Chemistry
저자 및
Ji Young Choi, Shyamsundar Das1, Dae Young Bae2, Eunsung Lee2, Byung Chul Lee3,*
Transdisciplinary Studies, Seoul National University, Korea
1Seoul National University Hospital, Korea
2Department of Chemistry, Pohang University of Science and Technology, Korea
3Department 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 [18F]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 CF3 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 CF3 substitution, [18F]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%, n ≥ 3) as well as [18F]CF3 substitution (72 ± 2.0%, n ≥ 3) as compared with reported ligand TMEDA (4.7 ± 0.7% and 44 ± 5.8%, n ≥ 3, respectively) [1]. In addition, [18F]trifluoromethylation of various aryl iodides obationed the desired products in moderate yields. The Cu ligand complex [(TMPhen)2Cu][COOCF2Cl] 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 CF3 substitution. This methodology applied for the synthesis of various [18F]trifluoromethyl substituted arene derivatives. [1] M. Huiban, M. Tredwell, S. Mizuta, Z. Wan, X. Zhang, T. L. Collier, V. Gouverneur, J. Passchier, Nat. Chem., 2013;5:941–944.