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 F NMR spectroscopy.
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Sodium-Catalyzed Friedel-Crafts Reactions and Mechanistic Insight.
Org Lett
June 2019
Department of Chemistry , University of California, One Shields Avenue , Davis , California 95616 , United States.
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 F NMR spectroscopy.
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