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Synthesis 2012(12): 1792-1797  
DOI: 10.1055/s-0031-1289715
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© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Direct Amination of Polyfluoroarenes and Azoles with Hydroxylamines and Its Application to the Synthesis of 3-Aminobenzoheteroles

Naoki Matsuda, Koji Hirano*, Tetsuya Satoh, Masahiro Miura*
Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
Fax: +81(6)68797362; e-Mail: k_hirano@chem.eng.osaka-u.ac.jp; miura@chem.eng.osaka-u.ac.jp;
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Publication History

Received 9 January 2012
Publication Date:
15 February 2012 (online)

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Abstract

A copper-catalyzed electrophilic, umpolung amination strategy for the direct C-H amination of polyfluoroarenes and 1,3-azoles has been developed. The copper-based amination reaction is robust and can be easily scaled up on a gram scale. Its application to an annulative electrophilic amination of o-alkynylphenols and -anilines for the synthesis of 3-aminobenzofurans and -indoles is also described.

Key words

copper - electrophilic amination - C-H functionalization - polyfluoroarenes - heterocycles