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

doi:10.1055/s-0031-1289715

PSP

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;

Abstract

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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

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