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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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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
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author Wagener, Tobias
Heusler, Arne
Nairoukh, Zackaria
Bergander, Klaus
Daniliuc, Constantin G.
Glorius, Frank
author_facet Wagener, Tobias
Heusler, Arne
Nairoukh, Zackaria
Bergander, Klaus
Daniliuc, Constantin G.
Glorius, Frank
author_sort Wagener, Tobias
collection PubMed
description [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.
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spelling pubmed-80400222021-04-13 Accessing (Multi)Fluorinated Piperidines Using Heterogeneous Hydrogenation Wagener, Tobias Heusler, Arne Nairoukh, Zackaria Bergander, Klaus Daniliuc, Constantin G. Glorius, Frank ACS Catal [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. American Chemical Society 2020-09-18 2020-10-16 /pmc/articles/PMC8040022/ /pubmed/33859866 http://dx.doi.org/10.1021/acscatal.0c03278 Text en This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (https://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Wagener, Tobias
Heusler, Arne
Nairoukh, Zackaria
Bergander, Klaus
Daniliuc, Constantin G.
Glorius, Frank
Accessing (Multi)Fluorinated Piperidines Using Heterogeneous Hydrogenation
title Accessing (Multi)Fluorinated Piperidines Using Heterogeneous Hydrogenation
title_full Accessing (Multi)Fluorinated Piperidines Using Heterogeneous Hydrogenation
title_fullStr Accessing (Multi)Fluorinated Piperidines Using Heterogeneous Hydrogenation
title_full_unstemmed Accessing (Multi)Fluorinated Piperidines Using Heterogeneous Hydrogenation
title_short Accessing (Multi)Fluorinated Piperidines Using Heterogeneous Hydrogenation
title_sort accessing (multi)fluorinated piperidines using heterogeneous hydrogenation
url 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
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