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

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 re...

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Published in:Angewandte Chemie International Edition 2011-06, Vol.50 (25), p.5674-5677
Main Authors: 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
Format: Article
Language:English
Subjects:
Amines
Amines - chemistry
Aniline Compounds - chemical synthesis
Aniline Compounds - chemistry
Benzene Derivatives - chemistry
benzynes
Electrons
nucleophilic addition
regioselective reactions
silicon
Silicon - chemistry
Stereoisomerism
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201100360