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Defluoroalkylation of Trifluoromethylarenes with Hydrazones: Rapid Access to Benzylic Difluoroarylethylamines

[Image: see text] Here, we report an efficient and modular approach toward the formation of difluorinated arylethylamines from simple aldehyde-derived N,N-dialkylhydrazones and trifluoromethylarenes (CF(3)-arenes). This method relies on selective C–F bond cleavage via reduction of the CF(3)-arene. W...

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Detalles Bibliográficos
Autores principales: Hendy, Cecilia M., Pratt, Cameron J., Jui, Nathan T., Blakey, Simon B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10012270/
https://www.ncbi.nlm.nih.gov/pubmed/36848497
http://dx.doi.org/10.1021/acs.orglett.3c00126
Descripción
Sumario:[Image: see text] Here, we report an efficient and modular approach toward the formation of difluorinated arylethylamines from simple aldehyde-derived N,N-dialkylhydrazones and trifluoromethylarenes (CF(3)-arenes). This method relies on selective C–F bond cleavage via reduction of the CF(3)-arene. We show that a diverse set of CF(3)-arenes and CF(3)-heteroarenes react smoothly with a range of aryl and alkyl hydrazones. The β-difluorobenzylic hydrazine product can be selectively cleaved to form the corresponding benzylic difluoroarylethylamines.