meta-Selective thiofluoroalkylation of substituted pyridines via Zincke imines

Will C. Hartley; Arnau Huerta; Júlia C. Negredo; Omar Boutureira

doi:10.1039/D5QO00533G

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meta-Selective thiofluoroalkylation of substituted pyridines via Zincke imines†

Will C. Hartley,

*^a Arnau Huerta,^a Júlia C. Negredo^a and Omar Boutureira

*^a

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* Corresponding authors

^a Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/Marcel·lí Domingo 1, 43007 Tarragona, Spain
E-mail: willconnor.hartley@urv.cat, omar.boutureira@urv.cat

Abstract

Zincke imines enable the regioselective thiofluoroalkylation of substituted pyridines, providing access to thioalkylated pyridines bearing a range of fluorination patterns. Crucial to the success of this strategy was the use of saccharine-derived thiofluoroalkylating reagents, which, upon reaction with TMSCl, generate electrophilic sulfenyl chlorides.

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Article information

DOI: https://doi.org/10.1039/D5QO00533G
Article type: Research Article
Submitted: 18 Mar 2025
Accepted: 23 Apr 2025
First published: 25 Apr 2025

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Org. Chem. Front., 2025, Advance Article

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meta-Selective thiofluoroalkylation of substituted pyridines via Zincke imines

W. C. Hartley, A. Huerta, J. C. Negredo and O. Boutureira, Org. Chem. Front., 2025, Advance Article , DOI: 10.1039/D5QO00533G

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meta-Selective thiofluoroalkylation of substituted pyridines via Zincke imines†

Abstract

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meta-Selective thiofluoroalkylation of substituted pyridines via Zincke imines

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