Palladium Nanoparticle-Catalyzed Stereoselective Domino Synthesis of All-Carbon Tetrasubstituted Olefin Containing Oxindoles via Carbopalladation/C–H Activation

The binaphthyl stabilized
palladium nanoparticles (Pd-BNP) catalyzed
single-step, stereoselective domino synthesis of symmetrically and
unsymmetrically all-carbon tetrasubstituted olefin containing oxindoles
from readily accessible anilides has been developed. The Pd-BNP catalyst
showed a wide range of functional group tolerance that enabled building
a library of heteroaromatics. This reusable Pd catalyst reflected
its utility in the synthesis of biologically important AMP-activated
protein kinase deprived of any metal Pd contamination. The nanocatalyst
was easily recovered and reused five times without any appreciable
loss in particle size or catalytic activity.