When facing the synthesis of highly electron deficient monoaryl, di-aryl and bis-diaryl acetonitriles, Christopher Gorman and his research group at North Carolina State University look at two different methods: Nucleophilic aromatic substitution (NAS) and palladium-mediated coupling.
In their search for the most efficient method, they show that palladium-mediated coupling is more efficient than nucleophilic aromatic substitution for cyano-containing, electron deficient molecules. They further show that choice of solvent, base and supporting ligand has a large effect on the yield of this coupling.
Read all of this in this HOT article that is free to access until the 31st March.
Overcoming challenges in the palladium-catalyzed synthesis of electron deficient ortho-substituted aryl acetonitriles
Molly C. Brannock, William J. Behof, Gregory Morrison and Christopher B. Gorman
Org. Biomol. Chem., 2011
DOI: 10.1039/C0OB00903B
