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Accessing (Multi)Fluorinated Piperidines Using Heterogeneous Hydrogenation.

ABSTRACT: 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.

SUBMITTER: Wagener T

PROVIDER: S-EPMC8040022 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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Accessing (Multi)Fluorinated Piperidines Using Heterogeneous Hydrogenation.

Wagener Tobias T Heusler Arne A Nairoukh Zackaria Z Bergander Klaus K Daniliuc Constantin G CG Glorius Frank F

ACS catalysis 20200918 20

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 <i>cis</i>-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. Fluor ...[more]

PMID: 33859866

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