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Accessing (Multi)Fluorinated Piperidines Using Heterogeneous Hydrogenation

[Image: see text] Fluorinated piperidines are desirable motifs for pharmaceutical and agrochemical research. Nevertheless, general synthetic access remains out of reach. Herein, we describe a simple and robust cis-selective hydrogenation of abundant and cheap fluoropyridines to yield a broad scope o...

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Detalles Bibliográficos
Autores principales: Wagener, Tobias, Heusler, Arne, Nairoukh, Zackaria, Bergander, Klaus, Daniliuc, Constantin G., Glorius, Frank
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8040022/
https://www.ncbi.nlm.nih.gov/pubmed/33859866
http://dx.doi.org/10.1021/acscatal.0c03278
Descripción
Sumario:[Image: see text] Fluorinated piperidines are desirable motifs for pharmaceutical and agrochemical research. Nevertheless, general synthetic access remains out of reach. Herein, we describe a simple and robust cis-selective hydrogenation of abundant and cheap fluoropyridines to yield a broad scope of (multi)fluorinated piperidines. This protocol enables the chemoselective reduction of fluoropyridines while tolerating other (hetero)aromatic systems using a commercially available heterogenous catalyst. Fluorinated derivatives of important drug compounds are prepared, and a straightforward strategy for the synthesis of enantioenriched fluorinated piperidines is disclosed.