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
a   USR 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
a   USR 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
a   USR 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
b   Inserm, CHU Lille, U1172-Lille Neuroscience & Cognition, Université de Lille, 59000 Lille, France
,
Christian Rolando
a   USR CNRS 3290, MSAP, Miniaturisation pour la Synthèse, l’Analyse et la Protéomique, Université de Lille, 59000 Lille, France   Email: laetitia.boissarie@univ-lille.fr
,
a   USR CNRS 3290, MSAP, Miniaturisation pour la Synthèse, l’Analyse et la Protéomique, Université de Lille, 59000 Lille, France   Email: laetitia.boissarie@univ-lille.fr
› Author Affiliations
This work was supported by the Centre National de la Recherche Scientifique (CNRS) and Université de Lille (PEPS 174920).


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.

Supporting Information



Publication History

Received: 10 July 2020

Accepted after revision: 02 September 2020

Article published online:
07 October 2020

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
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