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Mechanochemical Synthesis of Fluorinated Imines

A number of imines, including 12 new compounds, previously not reported in the literature, derived from variously fluorinated benzaldehydes and different anilines or chiral benzylamines were synthesized by a solvent-free mechanochemical method, which was based on the manual grinding of equimolar amo...

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Autores principales: Ciesielska, Karolina, Hoffmann, Marcin, Kubicki, Maciej, Pluskota-Karwatka, Donata
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9323187/
https://www.ncbi.nlm.nih.gov/pubmed/35889430
http://dx.doi.org/10.3390/molecules27144557
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author Ciesielska, Karolina
Hoffmann, Marcin
Kubicki, Maciej
Pluskota-Karwatka, Donata
author_facet Ciesielska, Karolina
Hoffmann, Marcin
Kubicki, Maciej
Pluskota-Karwatka, Donata
author_sort Ciesielska, Karolina
collection PubMed
description A number of imines, including 12 new compounds, previously not reported in the literature, derived from variously fluorinated benzaldehydes and different anilines or chiral benzylamines were synthesized by a solvent-free mechanochemical method, which was based on the manual grinding of equimolar amounts of the substrates at the room temperature. In a very short reaction time of only 15 min, the method produced the expected products with good-to-excellent yields. The yields were comparable or significantly higher than those reported in the literature for the imines synthesized by other methods. Importantly, the conditions used for the reactions with aniline derivatives also resulted in the high yields of imines obtained from chiral benzylamines, and can be extended to the synthesis with other similar amines. Structures of all imines were confirmed by NMR spectroscopy: (1)H, (13)C and (19)F. For four compounds, X-ray structures were also obtained. The synthetic approach presented in this paper contributes to the prevention of environmental pollution and can be easily extended for larger-scale syntheses. The mechanochemical solvent-free method provides a convenient strategy particularly useful for the preparation of fluorinated imines being versatile intermediates or starting material in the synthesis of drugs and other fine chemicals.
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spelling pubmed-93231872022-07-27 Mechanochemical Synthesis of Fluorinated Imines Ciesielska, Karolina Hoffmann, Marcin Kubicki, Maciej Pluskota-Karwatka, Donata Molecules Article A number of imines, including 12 new compounds, previously not reported in the literature, derived from variously fluorinated benzaldehydes and different anilines or chiral benzylamines were synthesized by a solvent-free mechanochemical method, which was based on the manual grinding of equimolar amounts of the substrates at the room temperature. In a very short reaction time of only 15 min, the method produced the expected products with good-to-excellent yields. The yields were comparable or significantly higher than those reported in the literature for the imines synthesized by other methods. Importantly, the conditions used for the reactions with aniline derivatives also resulted in the high yields of imines obtained from chiral benzylamines, and can be extended to the synthesis with other similar amines. Structures of all imines were confirmed by NMR spectroscopy: (1)H, (13)C and (19)F. For four compounds, X-ray structures were also obtained. The synthetic approach presented in this paper contributes to the prevention of environmental pollution and can be easily extended for larger-scale syntheses. The mechanochemical solvent-free method provides a convenient strategy particularly useful for the preparation of fluorinated imines being versatile intermediates or starting material in the synthesis of drugs and other fine chemicals. MDPI 2022-07-17 /pmc/articles/PMC9323187/ /pubmed/35889430 http://dx.doi.org/10.3390/molecules27144557 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Ciesielska, Karolina
Hoffmann, Marcin
Kubicki, Maciej
Pluskota-Karwatka, Donata
Mechanochemical Synthesis of Fluorinated Imines
title Mechanochemical Synthesis of Fluorinated Imines
title_full Mechanochemical Synthesis of Fluorinated Imines
title_fullStr Mechanochemical Synthesis of Fluorinated Imines
title_full_unstemmed Mechanochemical Synthesis of Fluorinated Imines
title_short Mechanochemical Synthesis of Fluorinated Imines
title_sort mechanochemical synthesis of fluorinated imines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9323187/
https://www.ncbi.nlm.nih.gov/pubmed/35889430
http://dx.doi.org/10.3390/molecules27144557
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