Pd-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols via capture of active tautomers

An efficient palladium-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols has been developed via capture of the active tautomers. A wide variety of 2,5-disubstituted and 2,4,5-trisubstituted pyrazolidinones have been synthesized with up to 96% and 95% ee, respectively. The hydr...

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Detalles Bibliográficos
Autores principales: Chen, Zhang-Pei, Chen, Mu-Wang, Shi, Lei, Yu, Chang-Bin, Zhou, Yong-Gui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5659069/
https://www.ncbi.nlm.nih.gov/pubmed/29511507
http://dx.doi.org/10.1039/c5sc00835b
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author Chen, Zhang-Pei
Chen, Mu-Wang
Shi, Lei
Yu, Chang-Bin
Zhou, Yong-Gui
author_facet Chen, Zhang-Pei
Chen, Mu-Wang
Shi, Lei
Yu, Chang-Bin
Zhou, Yong-Gui
author_sort Chen, Zhang-Pei
collection PubMed
description An efficient palladium-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols has been developed via capture of the active tautomers. A wide variety of 2,5-disubstituted and 2,4,5-trisubstituted pyrazolidinones have been synthesized with up to 96% and 95% ee, respectively. The hydrogenation pathway includes Brønsted acid promoted tautomerization of pyrazol-5-ols and Pd-catalyzed asymmetric hydrogenation of the active tautomer.
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spelling pubmed-56590692018-03-06 Pd-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols via capture of active tautomers Chen, Zhang-Pei Chen, Mu-Wang Shi, Lei Yu, Chang-Bin Zhou, Yong-Gui Chem Sci Chemistry An efficient palladium-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols has been developed via capture of the active tautomers. A wide variety of 2,5-disubstituted and 2,4,5-trisubstituted pyrazolidinones have been synthesized with up to 96% and 95% ee, respectively. The hydrogenation pathway includes Brønsted acid promoted tautomerization of pyrazol-5-ols and Pd-catalyzed asymmetric hydrogenation of the active tautomer. Royal Society of Chemistry 2015-06-01 2015-03-31 /pmc/articles/PMC5659069/ /pubmed/29511507 http://dx.doi.org/10.1039/c5sc00835b Text en This journal is © The Royal Society of Chemistry 2015 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Chen, Zhang-Pei
Chen, Mu-Wang
Shi, Lei
Yu, Chang-Bin
Zhou, Yong-Gui
Pd-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols via capture of active tautomers
title Pd-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols via capture of active tautomers
title_full Pd-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols via capture of active tautomers
title_fullStr Pd-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols via capture of active tautomers
title_full_unstemmed Pd-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols via capture of active tautomers
title_short Pd-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols via capture of active tautomers
title_sort pd-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols via capture of active tautomers
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5659069/
https://www.ncbi.nlm.nih.gov/pubmed/29511507
http://dx.doi.org/10.1039/c5sc00835b
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