No carrier-added nucleophilic aromatic radiofluorination using solid phase supported arenediazonium sulfonates and 1-(aryldiazenyl)piperazines

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• 作者：Patrick J. Riss^a ; ^{pr340@wbic.cam.ac.uk} ; Sonja Kuschel^a ; ^b ; Franklin I. Aigbirhio^a
• 关键词：Nucleophilic aromatic radiofluorination ; Fluorine-18 ; Solid phase ; Wallach reaction ; Balz&ndash ; Schiemann reaction
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：4 April, 2012
• 卷：53
• 期：14
• 页码：1717-1719
• 文件大小：408 K

摘要

This Letter concerns the investigation of a solid phase based method for no carrier-added nucleophilic [¹⁸F]fluorination of aromatic compounds via de-diazofluorination. Initial screening of reaction conditions was conducted using soluble analogues, that is, substituted benzenediazonium tosylates and 1-(phenyldiazenyl)piperazines in solution. This was followed by translation of the principle conditions to solid phase bound analogues. A variety of substituted aryldiazonium cations were immobilised using a sulfonate functionalised ion exchange resin and labelled with [¹⁸F]fluoride ion by Balz-Schiemann like thermal decomposition in the presence of no carrier-added [¹⁸F]fluoride ion. Likewise, a chloromethyl-bearing (Merrifield-) resin was modified using piperazine to provide the means for covalent immobilisation of diazonium ions. The resin bound 1-(aryldiazenyl)piperazines obtained were used as substrates for a Wallach reaction with hydrogen [¹⁸F]fluoride.