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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*

*Department of Chemistry and Chemical Engineering, Inha University, 100 Inha-ro, Nam-gu, Incheon 402-751, Korea, Email: kimdwinha.ac.kr

S. M. Kang, C. H. Kim, K. C. Lee, D. W. Kim, Org. Lett., 2019, 21, 3062-3066.

DOI: 10.1021/acs.orglett.9b00649 (free Supporting Information)


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Abstract

A bis-triethylene glycolic crown-5-calix[4]arene (BTC5A) is 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.

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Bis-triethylene glycol-functionalized crown-5-calix[4]arene (BTC5A) as a promoter of SN2 fluorination by KF.



Key Words

fluorination, SN2 reaction


ID: J54-Y2019