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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 20
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Original Articles

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

, , &
Pages 2999-3007 | Received 31 Mar 2014, Published online: 08 Aug 2014
 

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

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.

Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/lsyc.

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