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Intermolecular radical oxyalkylation of arynes with alkenes and TEMPO.

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.

SUBMITTER: Bhattacharya D

PROVIDER: S-EPMC11351772 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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Intermolecular radical oxyalkylation of arynes with alkenes and TEMPO.

Bhattacharya Debkanta D Scherübl Maximilian M Daniliuc Constantin G CG Studer Armido A

Chemical science 20240726 34

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 alkene ...[more]

PMID: 39211489

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