Bis-triethylene Glycolic Crown-5-calix[4]arene: A Promoter of Nucleophilic Fluorination Using Potassium Fluoride

Seok Min Kang; Chul Hee Kim; Kyo Chul Lee; Dong Wook Kim

doi:10.1021/acs.orglett.9b00649

Bis-triethylene Glycolic Crown-5-calix[4]arene: A Promoter of Nucleophilic Fluorination Using Potassium Fluoride

Seok Min Kang, Chul Hee Kim, Kyo Chul Lee, Dong Wook Kim

Research output: Contribution to journal › Article › peer-review

23 Scopus citations

Abstract

We designed and synthesized a bis-triethylene glycolic crown-5-calix[4]arene (BTC5A) as a multifunctional promoter for nucleophilic fluorination using KF. The synergetic effect of the calix-crown moiety and ethylene glycols of BTC5A enabled KF to be easily dissolved in organic solvents and activated the fluoride in even nonpolar aprotic media. To validate its practicality, the S _N 2 fluorinations including ¹⁸ F-fluorination of various substrates were successfully conducted using KF(or [ ¹⁸ F]F ^- ) in the presence of BTC5A.

Original language	English
Pages (from-to)	3062-3066
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.9b00649
State	Published - 3 May 2019

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© 2019 American Chemical Society.

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title = "Bis-triethylene Glycolic Crown-5-calix[4]arene: A Promoter of Nucleophilic Fluorination Using Potassium Fluoride",

abstract = " We designed and synthesized a bis-triethylene glycolic crown-5-calix[4]arene (BTC5A) as a multifunctional promoter for nucleophilic fluorination using KF. The synergetic effect of the calix-crown moiety and ethylene glycols of BTC5A enabled KF to be easily dissolved in organic solvents and activated the fluoride in even nonpolar aprotic media. To validate its practicality, the S N 2 fluorinations including 18 F-fluorination of various substrates were successfully conducted using KF(or [ 18 F]F - ) in the presence of BTC5A.",

author = "Kang, {Seok Min} and Kim, {Chul Hee} and Lee, {Kyo Chul} and Kim, {Dong Wook}",

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AU - Lee, Kyo Chul

AU - Kim, Dong Wook

PY - 2019/5/3

Y1 - 2019/5/3

N2 - We designed and synthesized a bis-triethylene glycolic crown-5-calix[4]arene (BTC5A) as a multifunctional promoter for nucleophilic fluorination using KF. The synergetic effect of the calix-crown moiety and ethylene glycols of BTC5A enabled KF to be easily dissolved in organic solvents and activated the fluoride in even nonpolar aprotic media. To validate its practicality, the S N 2 fluorinations including 18 F-fluorination of various substrates were successfully conducted using KF(or [ 18 F]F - ) in the presence of BTC5A.

AB - We designed and synthesized a bis-triethylene glycolic crown-5-calix[4]arene (BTC5A) as a multifunctional promoter for nucleophilic fluorination using KF. The synergetic effect of the calix-crown moiety and ethylene glycols of BTC5A enabled KF to be easily dissolved in organic solvents and activated the fluoride in even nonpolar aprotic media. To validate its practicality, the S N 2 fluorinations including 18 F-fluorination of various substrates were successfully conducted using KF(or [ 18 F]F - ) in the presence of BTC5A.

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Bis-triethylene Glycolic Crown-5-calix[4]arene: A Promoter of Nucleophilic Fluorination Using Potassium Fluoride

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