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Stereoselective Direct N‐Trifluoropropenylation of Heterocycles with a Hypervalent Iodonium Reagent

The availability and synthesis of fluorinated enamine derivatives such as N‐(3,3,3‐trifluoropropenyl)heterocycles are challenging, especially through direct functionalization of the heterocyclic scaffold. Herein, a stereoselective N‐trifluoropropenylation method based on the use of a bench‐stable tr...

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Autores principales: Csenki, János T., Mészáros, Ádám, Gonda, Zsombor, Novák, Zoltán
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9293340/
https://www.ncbi.nlm.nih.gov/pubmed/34549840
http://dx.doi.org/10.1002/chem.202102840
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author Csenki, János T.
Mészáros, Ádám
Gonda, Zsombor
Novák, Zoltán
author_facet Csenki, János T.
Mészáros, Ádám
Gonda, Zsombor
Novák, Zoltán
author_sort Csenki, János T.
collection PubMed
description The availability and synthesis of fluorinated enamine derivatives such as N‐(3,3,3‐trifluoropropenyl)heterocycles are challenging, especially through direct functionalization of the heterocyclic scaffold. Herein, a stereoselective N‐trifluoropropenylation method based on the use of a bench‐stable trifluoropropenyl iodonium salt is described. This reagent enables the straightforward trifluoropropenylation of various N‐heterocycles under mild reaction conditions, providing trifluoromethyl enamine type moieties with high stereoselectivity and efficiency.
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spelling pubmed-92933402022-07-20 Stereoselective Direct N‐Trifluoropropenylation of Heterocycles with a Hypervalent Iodonium Reagent Csenki, János T. Mészáros, Ádám Gonda, Zsombor Novák, Zoltán Chemistry Communications The availability and synthesis of fluorinated enamine derivatives such as N‐(3,3,3‐trifluoropropenyl)heterocycles are challenging, especially through direct functionalization of the heterocyclic scaffold. Herein, a stereoselective N‐trifluoropropenylation method based on the use of a bench‐stable trifluoropropenyl iodonium salt is described. This reagent enables the straightforward trifluoropropenylation of various N‐heterocycles under mild reaction conditions, providing trifluoromethyl enamine type moieties with high stereoselectivity and efficiency. John Wiley and Sons Inc. 2021-10-06 2021-11-11 /pmc/articles/PMC9293340/ /pubmed/34549840 http://dx.doi.org/10.1002/chem.202102840 Text en © 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Csenki, János T.
Mészáros, Ádám
Gonda, Zsombor
Novák, Zoltán
Stereoselective Direct N‐Trifluoropropenylation of Heterocycles with a Hypervalent Iodonium Reagent
title Stereoselective Direct N‐Trifluoropropenylation of Heterocycles with a Hypervalent Iodonium Reagent
title_full Stereoselective Direct N‐Trifluoropropenylation of Heterocycles with a Hypervalent Iodonium Reagent
title_fullStr Stereoselective Direct N‐Trifluoropropenylation of Heterocycles with a Hypervalent Iodonium Reagent
title_full_unstemmed Stereoselective Direct N‐Trifluoropropenylation of Heterocycles with a Hypervalent Iodonium Reagent
title_short Stereoselective Direct N‐Trifluoropropenylation of Heterocycles with a Hypervalent Iodonium Reagent
title_sort stereoselective direct n‐trifluoropropenylation of heterocycles with a hypervalent iodonium reagent
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9293340/
https://www.ncbi.nlm.nih.gov/pubmed/34549840
http://dx.doi.org/10.1002/chem.202102840
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