Transition-Metal-Free Electrophilic Amination between Aryl Grignard Reagents and N-Chloroamines
Takuji Hatakeyama, Yuya Yoshimoto, Sujit K. Ghorai and Masaharu Nakamura*
*International Research Center for Elements Science, Institute for Chemical Research, Graduate School of Engineering, Kyoto University, Uji, Kyoto, 611-0011, Japan, Email: masaharuscl.kyoto-u.ac.jp
T. Hatakeyama, Y. Yoshimoto, S. K. Ghorai, M. Nakamura, Org. Lett., 2010, 12, 1516-1519.
In the presence of N,N,N′,N′-tetramethylethylenediamine (TMEDA) as an additive, easily prepared and handled N-chloroamines react with aryl Grignard reagents to give various arylamines in good to excellent yields. Functional groups such as ester and nitrile are tolerated.
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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.