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

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

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8 Scopus citations

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-πinteractions. [18F]Flumazenil was produced in high radiochemical yield using M-BTC5A.

Original language	English
Pages (from-to)	9551-9555
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.0c03604
State	Published - 18 Dec 2020

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© 2020 American Chemical Society.

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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-πinteractions. [18F]Flumazenil was produced in high radiochemical yield using M-BTC5A.",

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AU - Lee, Won Chang

AU - Kang, Seok Min

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AU - Kim, Sang Eun

AU - Kim, Dong Wook

PY - 2020/12/18

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AB - 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-πinteractions. [18F]Flumazenil was produced in high radiochemical yield using M-BTC5A.

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

Abstract

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