1313182-85-2Relevant academic research and scientific papers
Regiocomplementary cycloaddition reactions of boryl- and silylbenzynes with 1,3-dipoles: Selective synthesis of benzo-fused azole derivatives
Ikawa, Takashi,Takagi, Akira,Goto, Masahiko,Aoyama, Yuya,Ishikawa, Yoshinobu,Itoh, Yuji,Fujii, Satoshi,Tokiwa, Hiroaki,Akai, Shuji
, p. 2965 - 2983 (2013/06/26)
Benzo-fused nitrogen-containing heterocycles are abundant in biologically active compounds. One of the most important methods for preparing such heterocycles is the (3 + 2) cycloaddition reaction of benzynes with 1,3-dipolar compounds. However, the reacti
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
