1313182-35-2Relevant academic research and scientific papers
Ortho-selective nucleophilic addition of primary amines to silylbenzynes: Synthesis of 2-silylanilines
Ikawa, Takashi,Nishiyama, Tsuyoshi,Shigeta, Takashi,Mohri, Shinya,Morita, Shinsuke,Takayanagi, Sho-Ichi,Terauchi, Yuki,Morikawa, Yuki,Takagi, Akira,Ishikawa, Yoshinobu,Fujii, Satoshi,Kita, Yasuyuki,Akai, Shuji
supporting information; experimental part, p. 5674 - 5677 (2011/08/06)
Cause and effect: The first ortho-selective nucleophilic addition reaction of amines to 3-substituted benzynes has been achieved. Despite a large trimethylsilyl substituent, primary amines attack the C2 position of 3-silylbenzynes to produce 2-silylanilines (see scheme). This outcome is likely to result from the inductive electron-donating effect of the silyl group, which overrides its steric repulsion with the approaching amines. Copyright
