Cargando…

NHC–BIAN–Cu(I)-Catalyzed Friedländer-Type Annulation of 2-Amino-3-(per)fluoroacetylpyridines with Alkynes on Water

[Image: see text] The direct catalytic alkynylation/dehydrative cyclization of 2-amino-3-trifluoroacetyl-pyridines on water was developed for the efficient synthesis of a broad range of fluorinated 1,8-naphthyridines from terminal alkynes. A novel N-heterocyclic carbene (NHC) ligand system that comb...

Descripción completa

Detalles Bibliográficos
Autores principales: Dolna, Magdalena, Nowacki, Michał, Danylyuk, Oksana, Brotons-Rufes, Artur, Poater, Albert, Michalak, Michał
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9087358/
https://www.ncbi.nlm.nih.gov/pubmed/35394784
http://dx.doi.org/10.1021/acs.joc.2c00380
_version_ 1784704187516321792
author Dolna, Magdalena
Nowacki, Michał
Danylyuk, Oksana
Brotons-Rufes, Artur
Poater, Albert
Michalak, Michał
author_facet Dolna, Magdalena
Nowacki, Michał
Danylyuk, Oksana
Brotons-Rufes, Artur
Poater, Albert
Michalak, Michał
author_sort Dolna, Magdalena
collection PubMed
description [Image: see text] The direct catalytic alkynylation/dehydrative cyclization of 2-amino-3-trifluoroacetyl-pyridines on water was developed for the efficient synthesis of a broad range of fluorinated 1,8-naphthyridines from terminal alkynes. A novel N-heterocyclic carbene (NHC) ligand system that combines a π-extended acenaphthylene backbone with sterically bulky pentiptycene pendant groups was successfully utilized in a copper- or silver-mediated cyclization. Computational analysis of the reaction pathway supports our explanation of the different experimental conversions and yields for the set of copper and silver catalysts. The impact of steric hindrance at the metal center and the flexibility of substituents on the imidazole ring of the NHC on catalytic performance are also discussed.
format Online
Article
Text
id pubmed-9087358
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-90873582022-05-11 NHC–BIAN–Cu(I)-Catalyzed Friedländer-Type Annulation of 2-Amino-3-(per)fluoroacetylpyridines with Alkynes on Water Dolna, Magdalena Nowacki, Michał Danylyuk, Oksana Brotons-Rufes, Artur Poater, Albert Michalak, Michał J Org Chem [Image: see text] The direct catalytic alkynylation/dehydrative cyclization of 2-amino-3-trifluoroacetyl-pyridines on water was developed for the efficient synthesis of a broad range of fluorinated 1,8-naphthyridines from terminal alkynes. A novel N-heterocyclic carbene (NHC) ligand system that combines a π-extended acenaphthylene backbone with sterically bulky pentiptycene pendant groups was successfully utilized in a copper- or silver-mediated cyclization. Computational analysis of the reaction pathway supports our explanation of the different experimental conversions and yields for the set of copper and silver catalysts. The impact of steric hindrance at the metal center and the flexibility of substituents on the imidazole ring of the NHC on catalytic performance are also discussed. American Chemical Society 2022-04-08 2022-05-06 /pmc/articles/PMC9087358/ /pubmed/35394784 http://dx.doi.org/10.1021/acs.joc.2c00380 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Dolna, Magdalena
Nowacki, Michał
Danylyuk, Oksana
Brotons-Rufes, Artur
Poater, Albert
Michalak, Michał
NHC–BIAN–Cu(I)-Catalyzed Friedländer-Type Annulation of 2-Amino-3-(per)fluoroacetylpyridines with Alkynes on Water
title NHC–BIAN–Cu(I)-Catalyzed Friedländer-Type Annulation of 2-Amino-3-(per)fluoroacetylpyridines with Alkynes on Water
title_full NHC–BIAN–Cu(I)-Catalyzed Friedländer-Type Annulation of 2-Amino-3-(per)fluoroacetylpyridines with Alkynes on Water
title_fullStr NHC–BIAN–Cu(I)-Catalyzed Friedländer-Type Annulation of 2-Amino-3-(per)fluoroacetylpyridines with Alkynes on Water
title_full_unstemmed NHC–BIAN–Cu(I)-Catalyzed Friedländer-Type Annulation of 2-Amino-3-(per)fluoroacetylpyridines with Alkynes on Water
title_short NHC–BIAN–Cu(I)-Catalyzed Friedländer-Type Annulation of 2-Amino-3-(per)fluoroacetylpyridines with Alkynes on Water
title_sort nhc–bian–cu(i)-catalyzed friedländer-type annulation of 2-amino-3-(per)fluoroacetylpyridines with alkynes on water
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9087358/
https://www.ncbi.nlm.nih.gov/pubmed/35394784
http://dx.doi.org/10.1021/acs.joc.2c00380
work_keys_str_mv AT dolnamagdalena nhcbiancuicatalyzedfriedlandertypeannulationof2amino3perfluoroacetylpyridineswithalkynesonwater
AT nowackimichał nhcbiancuicatalyzedfriedlandertypeannulationof2amino3perfluoroacetylpyridineswithalkynesonwater
AT danylyukoksana nhcbiancuicatalyzedfriedlandertypeannulationof2amino3perfluoroacetylpyridineswithalkynesonwater
AT brotonsrufesartur nhcbiancuicatalyzedfriedlandertypeannulationof2amino3perfluoroacetylpyridineswithalkynesonwater
AT poateralbert nhcbiancuicatalyzedfriedlandertypeannulationof2amino3perfluoroacetylpyridineswithalkynesonwater
AT michalakmichał nhcbiancuicatalyzedfriedlandertypeannulationof2amino3perfluoroacetylpyridineswithalkynesonwater