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Electrophilic Amination with Nitroarenes
Author(s) -
Rauser Marian,
Ascheberg Christoph,
Niggemann Meike
Publication year - 2017
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.201705356
Subject(s) - electrophilic amination , amination , electrophile , reagent , chemistry , combinatorial chemistry , organic chemistry , nitro , reductive amination , catalysis , alkyl
An exceptionally general electrophilic amination, which directly transforms commercially available nitroarenes into alkylated aromatic aminoboranes with zinc organyl compounds was developed. The reaction starts with a two‐step partial reduction of the nitro group to a nitrenoid, which is used in situ as the electrophilic amination reagent. To facilitate isolation, the resulting air‐ and moisture‐sensitive aminoboranes were reacted with a range of electrophiles. The method not only represents a direct transformation of nitro compounds into electrophilic amination reagents but also provides an elegant alternative to dehydrocoupling methods for the generation of aminoboranes.