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Iron-Catalyzed Aromatic Amination for Nonsymmetrical Triarylamine Synthesis

Takuji Hatakeyama, Ryuji Imayoshi, Yuya Yoshimoto, Sujit K. Ghorai, Masayoshi Jin, Hikaru Takaya, Kazuhiro Norisuye, Yoshiki Sohrin and Masaharu Nakamura*

*International Research Center for Elements Science (IRCELS), Institute for Chemical Research (ICR), Kyoto University, Uji, Kyoto, 611-0011, Japan, Email: masaharuscl.kyoto-u.ac.jp

T. Hatakeyama, R. Imayoshi, Y. Yoshimoto, S. K. Ghorai, M. Jin, H. Takaya, K. Norisuye, Y. Sohrin, M. Nakamura, J. Am. Chem. Soc., 2012, 134, 20262-20265.

DOI: 10.1021/ja309845k (free Supporting Information)


Abstract

The use of in situ generated magnesium amides in the presence of a lithium halide dramatically increases the product yield of iron-catalyzed amination reactions. The present method is simple and free of precious and expensive metals and ligands and provides a convenient route to triarylamines, a recurrent core unit in organic electronic materials as well as pharmaceuticals.

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Transition-Metal-Free Electrophilic Amination between Aryl Grignard Reagents and N-Chloroamines

T. Hatakeyama, Y. Yoshimoto, S. K. Ghorai, M. Nakamura, Org. Lett., 2010, 12, 1516-1519.


Key Words

aryl amines


ID: J48-Y2012-3820