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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...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American
Chemical Society
2020
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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. |
format | Online Article Text |
id | pubmed-8040022 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American
Chemical Society |
record_format | MEDLINE/PubMed |
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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