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.
DOI: 10.1021/ol100235b (free Supporting Information)
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.
see article for more examples
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.