Cooperative N-Heterocyclic Carbene/Nickel-Catalyzed Hydroacylation of 1,3-Dienes with Aldehydes in Water

The cooperative N-heterocyclic carbene/nickel-catalyzed redox-neutral hydroacylation of 1,3-dienes with aldehydes in water was reported. A wide range of aliphatic and aromatic aldehydes were directly coupled with 1,3-dienes, providing synthetically useful beta,gamma-unsaturated ketones or the corresponding ketones after hydrogenation in moderate to high yields and high atom economy. This protocol first demonstrated the compatibility of NHC catalysis with nickel catalysis. Water was used as the sole solvent, which is rarely reported in a cooperative metal/organic catalytic system.

Automated summary

The cooperative N-heterocyclic carbene/nickel-catalyzed redox-neutral hydroacylation of 1,3-dienes with aldehydes in water was successfully achieved, providing synthetically useful compounds with high atom economy. This study demonstrated the compatibility of NHC catalysis with nickel catalysis and utilized water as the sole solvent, which is rarely reported in cooperative metal/organic catalytic systems.