Directed Palladium Catalyzed C−H (Ethoxycarbonyl)difluoromethylthiolation Reactions

The unprecedented Pd‐catalyzed (ethoxycarbonyl)difluoromethylthiolation reaction of various unsaturated derivatives was studied. In the presence of the (ethoxycarbonyl)difluoromethylsulfenamide reagent I and under mild reaction conditions (60 °C), both 2‐(hetero)aryl and 2‐(α‐aryl‐vinyl)pyridine der...

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Autores principales: Doche, Floriane, Escudero, Julien, Petit‐Cancelier, Fabien, Xiong, Heng‐Ying, Couve‐Bonnaire, Samuel, Audisio, Davide, Poisson, Thomas, Besset, Tatiana
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9826264/
https://www.ncbi.nlm.nih.gov/pubmed/35904010
http://dx.doi.org/10.1002/chem.202202099
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author Doche, Floriane
Escudero, Julien
Petit‐Cancelier, Fabien
Xiong, Heng‐Ying
Couve‐Bonnaire, Samuel
Audisio, Davide
Poisson, Thomas
Besset, Tatiana
author_facet Doche, Floriane
Escudero, Julien
Petit‐Cancelier, Fabien
Xiong, Heng‐Ying
Couve‐Bonnaire, Samuel
Audisio, Davide
Poisson, Thomas
Besset, Tatiana
author_sort Doche, Floriane
collection PubMed
description The unprecedented Pd‐catalyzed (ethoxycarbonyl)difluoromethylthiolation reaction of various unsaturated derivatives was studied. In the presence of the (ethoxycarbonyl)difluoromethylsulfenamide reagent I and under mild reaction conditions (60 °C), both 2‐(hetero)aryl and 2‐(α‐aryl‐vinyl)pyridine derivatives were smoothly functionalized with this methodology (37 examples, up to 87 % yield). Moreover, the synthetic interest of this fluorinated moiety was further showcased by its conversion into various original fluorinated residues. Finally, a plausible mechanism for this transformation was suggested.
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spelling pubmed-98262642023-01-09 Directed Palladium Catalyzed C−H (Ethoxycarbonyl)difluoromethylthiolation Reactions Doche, Floriane Escudero, Julien Petit‐Cancelier, Fabien Xiong, Heng‐Ying Couve‐Bonnaire, Samuel Audisio, Davide Poisson, Thomas Besset, Tatiana Chemistry Research Articles The unprecedented Pd‐catalyzed (ethoxycarbonyl)difluoromethylthiolation reaction of various unsaturated derivatives was studied. In the presence of the (ethoxycarbonyl)difluoromethylsulfenamide reagent I and under mild reaction conditions (60 °C), both 2‐(hetero)aryl and 2‐(α‐aryl‐vinyl)pyridine derivatives were smoothly functionalized with this methodology (37 examples, up to 87 % yield). Moreover, the synthetic interest of this fluorinated moiety was further showcased by its conversion into various original fluorinated residues. Finally, a plausible mechanism for this transformation was suggested. John Wiley and Sons Inc. 2022-09-13 2022-11-16 /pmc/articles/PMC9826264/ /pubmed/35904010 http://dx.doi.org/10.1002/chem.202202099 Text en © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Research Articles
Doche, Floriane
Escudero, Julien
Petit‐Cancelier, Fabien
Xiong, Heng‐Ying
Couve‐Bonnaire, Samuel
Audisio, Davide
Poisson, Thomas
Besset, Tatiana
Directed Palladium Catalyzed C−H (Ethoxycarbonyl)difluoromethylthiolation Reactions
title Directed Palladium Catalyzed C−H (Ethoxycarbonyl)difluoromethylthiolation Reactions
title_full Directed Palladium Catalyzed C−H (Ethoxycarbonyl)difluoromethylthiolation Reactions
title_fullStr Directed Palladium Catalyzed C−H (Ethoxycarbonyl)difluoromethylthiolation Reactions
title_full_unstemmed Directed Palladium Catalyzed C−H (Ethoxycarbonyl)difluoromethylthiolation Reactions
title_short Directed Palladium Catalyzed C−H (Ethoxycarbonyl)difluoromethylthiolation Reactions
title_sort directed palladium catalyzed c−h (ethoxycarbonyl)difluoromethylthiolation reactions
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9826264/
https://www.ncbi.nlm.nih.gov/pubmed/35904010
http://dx.doi.org/10.1002/chem.202202099
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