Direct and Regioselective C(sp3)–H Bond Fluorination of 2-Alkylazaarenes with Selectfluor

Clothilde Le Guen; Ahmed Mazzah; Maël Penhoat; Patricia Melnyk; Christian Rolando; Laëtitia Chausset-Boissarie

doi:10.1055/s-0040-1706482

Synthesis, Table of Contents

Synthesis 2021; 53(06): 1157-1162
DOI: 10.1055/s-0040-1706482

paper

Direct and Regioselective C(sp³)–H Bond Fluorination of 2-Alkylazaarenes with Selectfluor

Clothilde Le Guen

^aUSR CNRS 3290, MSAP, Miniaturisation pour la Synthèse, l’Analyse et la Protéomique, Université de Lille, 59000 Lille, France Email: laetitia.boissarie@univ-lille.fr

,

Ahmed Mazzah

^aUSR CNRS 3290, MSAP, Miniaturisation pour la Synthèse, l’Analyse et la Protéomique, Université de Lille, 59000 Lille, France Email: laetitia.boissarie@univ-lille.fr

,

Maël Penhoat

^aUSR CNRS 3290, MSAP, Miniaturisation pour la Synthèse, l’Analyse et la Protéomique, Université de Lille, 59000 Lille, France Email: laetitia.boissarie@univ-lille.fr

,

Patricia Melnyk

^bInserm, CHU Lille, U1172-Lille Neuroscience & Cognition, Université de Lille, 59000 Lille, France

,

Christian Rolando

^aUSR CNRS 3290, MSAP, Miniaturisation pour la Synthèse, l’Analyse et la Protéomique, Université de Lille, 59000 Lille, France Email: laetitia.boissarie@univ-lille.fr

,

Laëtitia Chausset-Boissarie ∗

^aUSR CNRS 3290, MSAP, Miniaturisation pour la Synthèse, l’Analyse et la Protéomique, Université de Lille, 59000 Lille, France Email: laetitia.boissarie@univ-lille.fr

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Abstract

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Abstract

Herein, a regioselective and direct monofluorination strategy of pyridylic and quinolinic C(sp³)–H bonds was developed under transition-metal-free conditions with Selectfluor. The reaction was performed under smooth conditions and afforded fluorinated azaheterocycles including 2-methylpyridines and -quinolines in moderate to good yields.

Key words

fluorination - azaheterocycle - Selectfluor - 2-methylpyridines - 2-methylquinolines

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References

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