Accessing (Multi)Fluorinated Piperidines Using Heterogeneous Hydrogenation

Tobias Wagener, Arne Heusler, Zackaria Nairoukh, Klaus Bergander, Constantin G. Daniliuc, Frank Glorius*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

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.

Original languageAmerican English
Pages (from-to)12052-12057
Number of pages6
JournalACS Catalysis
Volume10
Issue number20
DOIs
StatePublished - 16 Oct 2020
Externally publishedYes

Bibliographical note

Publisher Copyright:
Copyright © 2020 American Chemical Society.

Keywords

  • fluorine
  • heterogeneous catalysis
  • hydrogenation
  • nitrogen heterocycles
  • palladium

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