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Accessing (Multi)Fluorinated Piperidines Using Heterogeneous Hydrogenation.

Tobias Wagener¹, Arne Heusler¹, Zackaria Nairoukh¹

¹Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, 48149 Münster, Germany.

|April 16, 2021

Summary

This summary is machine-generated.

Researchers developed a new method for synthesizing fluorinated piperidines from fluoropyridines using cis-selective hydrogenation. This breakthrough provides broad access to valuable fluorinated compounds for drug discovery and agrochemical research.

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Published on: June 24, 2022

Area of Science:

Organic Chemistry
Medicinal Chemistry
Catalysis

Background:

Fluorinated piperidines are crucial building blocks in pharmaceutical and agrochemical industries.
Existing synthetic routes for fluorinated piperidines are limited and lack generality.

Purpose of the Study:

To develop a simple, robust, and cis-selective method for synthesizing diverse fluorinated piperidines.
To enable the efficient preparation of fluorinated motifs for drug development.

Main Methods:

Utilized cis-selective hydrogenation of readily available fluoropyridines.
Employed a commercially available heterogeneous catalyst for chemoselective reduction.
Demonstrated tolerance of other (hetero)aromatic systems during the reaction.

Main Results:

Achieved a broad scope of (multi)fluorinated piperidines with high cis-selectivity.
Successfully synthesized fluorinated derivatives of important drug compounds.
Developed a straightforward strategy for enantioenriched fluorinated piperidines.

Conclusions:

The developed hydrogenation protocol offers a general and efficient synthetic access to valuable fluorinated piperidines.
This method facilitates the incorporation of fluorinated piperidine scaffolds into drug candidates.
The strategy opens new avenues for the synthesis of chiral fluorinated compounds.