5 years ago

Umpolung Addition of Aldehydes to Aryl Imines

Umpolung Addition of Aldehydes to Aryl Imines
Chao-Jun Li, Ning Chen, Haining Wang, Xi-Jie Dai
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. Hydrazine mediates the reductive coupling of aldehydes and aryl imines in the presence of a ruthenium(II) precatalyst and a bidentate phosphine ligand. This alternative approach to amine synthesis involves aldehyde-derived alkyl carbanion equivalents, enables the synthesis of a wide array of secondary amines in moderate to good yields, and tolerates various functional groups.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201610578

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