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ortho ‐Selective Nucleophilic Addition of Primary Amines to Silylbenzynes: Synthesis of 2‐Silylanilines

2011; Wiley; Volume: 50; Issue: 25 Linguagem: Inglês

10.1002/anie.201100360

1521-3773

Takashi Ikawa, Tsuyoshi Nishiyama, Takashi Shigeta, Shinya Mohri, Shinsuke Morita, Sho‐ichi Takayanagi, Yuki Terauchi, Yuki Morikawa, Akira Takagi, Yoshinobu Ishikawa, Satoshi Fujii, Yasuyuki Kita, Shuji Akai,

Coordination Chemistry and Organometallics

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.