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Catalyst‐Free Reductive Coupling of Aromatic and Aliphatic Nitro Compounds with Organohalides
Author(s) -
Rauser Marian,
Eckert Raphael,
Gerbershagen Max,
Niggemann Meike
Publication year - 2019
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.201814197
Subject(s) - nitro , chemistry , catalysis , aryl , halide , reactivity (psychology) , organic chemistry , aryl halide , medicinal chemistry , combinatorial chemistry , palladium , medicine , alkyl , alternative medicine , pathology
A rare reductive coupling of nitro compounds with organohalides has been realized. The reaction is initiated by a partial reduction of the nitro group to a nitrenoid intermediate. Therefore, not only aromatic but also aliphatic nitro compounds are efficiently transformed into monoalkylated amines, with organohalides as the alkylating agent. Given the innate reactivity of the nitrenoid, a catalyst is not required, resulting in a high tolerance for aryl halide substituents in both starting materials.