Tandem superelectrophilic activation for the regioselective chlorofluorination of recalcitrant allylic amines

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• 作者：Alexandre Le Darz^a ; ^b ; ^&dagger ; ; Ugo Castelli^a ; Naima Mokhtari^a ; Agnè ; s Martin-Mingot^a ; Jé ; rô ; me Marrot^c ; Fodil Bouazza^b ; ^&dagger ; ; Omar Karam^b ; ^&dagger ; ; Sé ; bastien Thibaudeau^a ; ^{sebastien.thibaudeau@univ-poitiers.fr" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Superacid chemistry ; Fluorine chemistry ; Halogenation
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：4 February 2016
• 年：2016
• 卷：72
• 期：5
• 页码：674-689
• 全文大小：1395 K

文摘

An efficient and straightforward regio-controlled route to β-fluoro-γ-chlorinated amines was developed via an ammonium–chloronium superelectrophilic activation in superacid HF/SbF₅. Through halogen directing effect the method was extended to a variety of (poly)halofluorinated building blocks amenable for further synthetic modifications. The direct synthesis of chlorofluorinated analogues of bioactive compounds via this process confirmed the ability to use this strategy for further applications in medicinal chemistry.