Sodium-Catalyzed Friedel-Crafts Reactions and Mechanistic Insight.

Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (NaBArF) demonstrates catalytic activity for Friedel-Crafts addition reactions of phenolic and other aromatic nucleophiles to trans-β-nitrostyrene. Solubility studies demonstrate a chelating effect between the Na+ cation and the nitro group of trans-β-nitrostyrene as the basis for catalytic activation. Mechanistic studies are presented, including a comparison with other sodium salts, additive effects, and reaction progress kinetics analysis using 19F NMR spectroscopy.