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J Am Chem Soc. 2013 Apr 3;135(13):5000-3. doi: 10.1021/ja402083e. Epub 2013 Mar 22.

Electrochemical C-H amination: synthesis of aromatic primary amines via N-arylpyridinium ions.

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1
Department of Synthetic Chemistry, Biological Chemistry, Graduate School of Engineering, Kyoto University , Nishikyo-ku, Kyoto 615-8510, Japan.

Abstract

We have developed a new method for C-H amination of aromatic compounds based on electrochemical oxidation of aromatic compounds in the presence of pyridine followed by the reaction of the resulting N-arylpyridinium ions with an alkylamine. This new transformation serves as a powerful method for synthesizing aromatic primary amines from aromatic compounds without using metal catalysts and harsh chemical reagents. High chemoselectivity of the present method is demonstrated by C-H amination of aromatic compounds bearing a nitro group to give a key intermediate for the synthesis of VLA-4 antagonist.

PMID:
23510504
DOI:
10.1021/ja402083e
[Indexed for MEDLINE]
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