A Simple and General Nickel-Catalyzed Michael-Type Hydroamination of Activated Olefins Using Arylamines

A simple and general addition of aromatic amines to activated olefins viz; acrylonitrile, phenyl vinyl sulfone and dimethyl maleate were realized using a combination of 1-10 mol% of NiBr2 and 2-20 mol% of AgOTf at 27-100 degrees C in toluene as solvent. A variety of aromatic amines bearing both electron donating and electron withdrawing groups including sterically demanding ones, as well as heteroaromatic amines could be added to activated olefins giving rise to the desired beta-amino acid derivatives or beta-amino sulfones in good yields. Addition of anilines to acrylonitrile was also found to be progressing when AgOTf alone was used as catalyst but was far less effective when compared to catalysis in the presence of NiBr2.

Automated summary

In this study, a simple and effective method for the addition of aromatic amines to activated olefins was discovered. The combination of NiBr2 and AgOTf catalysts resulted in high yields of the desired products, allowing for the addition of aromatic amines with various electron-donating and electron-withdrawing groups.