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双三甘醇冠醚-5-杯[4]芳烃：一种使用氟化钾进行亲核氟化反应的促进剂。

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

作者信息

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

机构信息

Department of Chemistry and Chemical Engineering , Inha University , 100 Inha-ro , Nam-gu, Incheon 402-751 , Korea.

Molecular Imaging Research Center , Korea Institute of Radiological and Medical Sciences , 75 Nowon-ro , Nowon-gu, Seoul 139-706 , Korea.

出版信息

Org Lett. 2019 May 3;21(9):3062-3066. doi: 10.1021/acs.orglett.9b00649. Epub 2019 Apr 16.

DOI:10.1021/acs.orglett.9b00649
PMID:30990693
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 S2 fluorinations including F-fluorination of various substrates were successfully conducted using KF(or [F]F) in the presence of BTC5A.

摘要

我们设计并合成了一种双三甘醇冠-5-杯[4]芳烃（BTC5A），作为使用KF进行亲核氟化的多功能促进剂。杯芳烃-冠醚部分和BTC5A的乙二醇的协同作用使KF能够轻松溶解于有机溶剂中，甚至在非极性非质子介质中也能活化氟化物。为了验证其实用性，在BTC5A存在下，使用KF（或[F]F）成功进行了包括各种底物的S2氟化反应。

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