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Updated: Jun 14, 2025

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Intermolecular radical oxyalkylation of arynes with alkenes and TEMPO
Debkanta Bhattacharya1, Maximilian Scherübl1, Constantin G Daniliuc1
1Organisch-Chemisches Institut, Universität Münster Corrensstraße 40 48149 Münster Germany studer@uni-muenster.de.
Abstract:
Radical transformations with arynes represent an underexplored research field and only a few examples have been disclosed. In this research article, the implementation of arynes in three-component reactions with TEMPO (2,2,6,6-tetramethylpiperidine 1-oxyl) and activated alkenes is demonstrated. TEMPO is added to arynes, which triggers a Meerwein-type arylation cascade where the final alkyl radial is eventually trapped by a second equivalent of TEMPO. This method is applicable to activated alkenes such as electron-deficient acrylates, styrenes and also vinyl acetate to provide various bisalkoxyamines. This work is a contribution to the emerging field of radical aryne chemistry.
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