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Nickel-catalyzed cross-electrophile coupling of 2-chloropyridines with alkyl bromides.

ABSTRACT: The synthesis of 2-alkylated pyridines by the nickel-catalyzed cross-coupling of two different electrophiles, 2-chloropyridines with alkyl bromides, is described. Compared to our previously published conditions for aryl halides, this method uses the different, more rigid bathophenanthroline ligand and is conducted at high concentration in DMF solvent. The method displays promising functional group compatibility and the conditions are orthogonal to the Stille coupling.

SUBMITTER: Everson DA 

PROVIDER: S-EPMC4006914 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature

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Nickel-catalyzed cross-electrophile coupling of 2-chloropyridines with alkyl bromides.

Everson Daniel A DA   Buonomo Joseph A JA   Weix Daniel J DJ  

Synlett : accounts and rapid communications in synthetic organic chemistry 20140101 2

The synthesis of 2-alkylated pyridines by the nickel-catalyzed cross-coupling of two different electrophiles, 2-chloropyridines with alkyl bromides, is described. Compared to our previously published conditions for aryl halides, this method uses the different, more rigid bathophenanthroline ligand and is conducted at high concentration in DMF solvent. The method displays promising functional group compatibility and the conditions are orthogonal to the Stille coupling. ...[more]

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