Catalytic C(sp2)-C(sp3) Bond Formation of Methoxyarenes by the Organic Superbase t-Bu-P4.

The organic superbase catalyst t-Bu-P4 achieves nucleophilic aromatic substitution of methoxyarenes with alkanenitrile pronucleophiles. A variety of functional groups [cyano, nitro, (non)enolizable ketone, chloride, and amide moieties] are allowed on methoxyarenes. Moreover, an array of alkanenitriles with/without an aryl moiety at the nitrile α-position can be employed. The system also features no requirement of a stoichiometric base, MeOH (not salt waste) formation as a byproduct, and the production of congested quaternary carbon centers.