Nickel-Catalyzed Reductive Alkylation of Halogenated Pyridines with Secondary Alkyl Bromides

Abstract

This article highlights Ni-catalyzed cross-electrophile coupling of halogenated pyridines with secondary alkyl bromides using zinc as the terminal reductant. With this protocol, we have successfully achieved different alkyl-substituted pyridines in moderate to excellent yields.

GRAPHICAL ABSTRACT

Keywords:

• Alkylation
• cross-coupling
• Ni-catalyzed
• pyridines
• zinc

Notes

^a Reaction conditions: 1a (0.15 mmol, 100 mol%), 2a (0.30 mmol, 200 mol%), NiBr₂ (10 mol%), ligand (10 mol%), Zn (300 mol%), Bu₄NBr (50 mol%), MgCl₂ (0.15 mmol)–pyridine (1:1), and DMA (1 mL).

^b Isolated yield.

^c 20% ligand was used.

^a Reaction conditions: alkyl bromide (0.15 mmol), halogenated pyridine (0.30 mmol, 200 mol%), NiBr₂ (10 mol%), ligand (10 mol%), Zn (300 mol%), Bu₄NBr (50 mol%), MgCl₂ (0.15 mmol)–pyridine (1:1), DMA (1 mL).

^b Isolated yield.

Authors Huiyan Liu and Zhuye Liang contributed equally to this work.

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