Multifunctional Crown-5-calix[4]arene-based Phase-Transfer Catalysts for Aromatic 18F-Fluorination

Won Chang Lee; Seok Min Kang; Byung Chul Lee; Sang Eun Kim; Dong Wook Kim

doi:10.1021/acs.orglett.0c03604

Multifunctional Crown-5-calix[4]arene-based Phase-Transfer Catalysts for Aromatic ¹⁸F-Fluorination

Org Lett. 2020 Dec 18;22(24):9551-9555. doi: 10.1021/acs.orglett.0c03604. Epub 2020 Dec 3.

Authors

Won Chang Lee^{1

2}, Seok Min Kang³, Byung Chul Lee^{1

4}, Sang Eun Kim^{1

4

5}, Dong Wook Kim³

Affiliations

¹ Department of Nuclear Medicine, Seoul National University Hospital, Seongnam 13620, Republic of Korea.
² Department of Transdisciplinary Studies, Graduate School of Convergence Science and Technology, Seoul National University, Seoul 08826, Republic of Korea.
³ Department of Chemistry and Chemical Engineering, Inha University, Incheon 22212, Republic of Korea.
⁴ Center for Nanomolecular Imaging and Innovative Drug Development, Advanced institutes of Convergence Technology, Suwon 16229, Republic of Korea.
⁵ Department of Molecular and Biophamaceutical Sciences, Graduate School of Convergence Science and Technology, Seoul National University, Seoul 08826, Republic of Korea.

PMID: 33270463
DOI: 10.1021/acs.orglett.0c03604

Abstract

Methylated bis-triethylene glycolic crown-5-calix[4]arene (M-BTC5A) as a phase-transfer catalyst showed the best performance among other analogues and even conventional Kryptofix 222 in the nucleophilic aromatic ¹⁸F-fluorination of diaryliodonium tosylate precursors owing to (i) the efficient release of reactive "naked" [¹⁸F]fluoride, (ii) the high stabilization of the precursor in the reaction, and, presumably, (iii) the ease of access between the precursor and the K¹⁸F/M-BTC5A complex facilitated by π-π interactions. [¹⁸F]Flumazenil was produced in high radiochemical yield using M-BTC5A.

Publication types

Research Support, Non-U.S. Gov't