Anion-catalyzed Phase-transfer Catalysis. I. Application to Diazo-coupling Reactions

Article abstract of DOI:10.1246/bcsj.56.796

Anion-catalyzed phase-transfer catalysis was evidenced in the diazo-coupling reactions of the arenediazonium ion with a range of diazophile components in liquid-liquid- and liquid-solid two-phase systems.The tetrakis<3,5-bis(trifluoromethyl)phenyl>borate ion was effective as an anionic catalyst to accelerate the reactions.Comparisons of the reaction rates in the two-phase system with those in solution systems indicated that the acceleration was due to the increased activity of the cationic reagent, partly by solubilization and partly by the dehydration of such cationic species in the nonpolar organic phase.