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Umpolung Addition of Aldehydes to Aryl Imines
Author(s) -
Chen Ning,
Dai XiJie,
Wang Haining,
Li ChaoJun
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.201610578
Subject(s) - carbanion , umpolung , chemistry , aryl , hydrazine (antidepressant) , alkyl , organic chemistry , ruthenium , combinatorial chemistry , catalysis , medicinal chemistry , nucleophile , chromatography
Abstract One of the classical ways to synthesize amines involves the coupling of carbonyl compounds and imines, either through enolate chemistry or acyl‐based carbanion equivalents. We herein report an alternative strategy that is based on the use of aldehydes as alkyl carbanion equivalents in a reductive coupling with aryl imines. A wide array of secondary amines can be synthesized in moderate to high yields. This reaction is mediated by hydrazine and catalyzed by ruthenium(II) complexes, and it tolerates various functional groups, such as esters, amides, and nitriles.