Synthesis of ß-Ketonitriles via N-Heterocyclic-Carbene-Catalyzed Radical Coupling of Aldehydes and Azobis(isobutyronitrile).

ABSTRACT

Herein, an NHC (N-heterocyclic carbene)-catalyzed radical coupling reaction between aldehydes and azobis(isobutyronitrile) (AIBN) has been developed. This method provides an efficient and convenient approach for the synthesis of ß-ketonitriles containing a quaternary carbon center (31 examples, up to >99% yield) utilizing commercially available substrates. This protocol features broad substrate scope, good functional group tolerance, and high efficiency under metal-free and mild reaction conditions.