Synthesis of 2-Arylpyridines and 2-Arylbipyridines via Photoredox-Induced Meerwein Arylation with in Situ Diazotization of Anilines

Wided Hagui (1) , Jean-François Soulé (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

We report herein a sustainable method for the preparation of 2-arylpyridines through C-H arylation of pyridines using in situ formed diazonium salts (from commercially available aromatic amines) in the presence of a photoredox catalyst under blue light-emitting diode (LED) irradiation. The reaction is tolerant to a wide range of functional groups (e.g., halogen, nitrile, formyl, acetyl, ester). Applications to the C-H bond arylation of bipyridine ligands is also presented.

Domaines: Chimie organique

Wided Hagui, Jean-François Soulé. Synthesis of 2-Arylpyridines and 2-Arylbipyridines via Photoredox-Induced Meerwein Arylation with in Situ Diazotization of Anilines. Journal of Organic Chemistry, 2020, 85 (5), pp.3655-3663. ⟨10.1021/acs.joc.9b03306⟩. ⟨hal-02498787⟩