Nickel-catalyzed reductive aminocarbonylation of vinyl triflates with nitro compounds for the synthesis of α,β-unsaturated amides

A nickel-catalyzed reductive aminocarbonylation reaction for the synthesis of alpha,beta-unsaturated amides has been described. By employing vinyl triflates and nitroarenes as readily available starting materials, a wide range of alpha,beta-unsaturated amide products were obtained in moderate to excellent yields with very good functional group tolerance in the absence of an external reductant. Notably, this is the first example of carbonylative synthesis of alpha,beta-unsaturated amides by applying a Ni/Mo(CO)(6) catalytic system with nitroarenes as promising nitrogen precursors. In addition, a late-stage modification of natural products was also achieved via this reductive aminocarbonylation approach.

Automated summary

A nickel-catalyzed reductive aminocarbonylation reaction has been developed for the synthesis of alpha,beta-unsaturated amides, using vinyl triflates and nitroarenes as starting materials. The method shows excellent functional group tolerance and can achieve high yields of the desired products. This study also demonstrates a potential late-stage modification strategy for natural products using the reductive aminocarbonylation approach.