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ortho ‐Selective Nucleophilic Addition of Primary Amines to Silylbenzynes: Synthesis of 2‐Silylanilines
Author(s) -
Ikawa Takashi,
Nishiyama Tsuyoshi,
Shigeta Takashi,
Mohri Shinya,
Morita Shinsuke,
Takayanagi Shoichi,
Terauchi Yuki,
Morikawa Yuki,
Takagi Akira,
Ishikawa Yoshinobu,
Fujii Satoshi,
Kita Yasuyuki,
Akai Shuji
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201100360
Subject(s) - steric effects , silylation , nucleophile , substituent , aryne , chemistry , primary (astronomy) , trimethylsilyl , nucleophilic addition , medicinal chemistry , stereochemistry , organic chemistry , catalysis , physics , astronomy
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.