The aqueous solutions of cationic surfactants (<i>e.g.</i>, cetyltrimethylammonium bromide; CTAB) at optimum concentrations were demonstrated to be effective in micellar catalysis of nucleophilic aromatic substitution reactions giving fast and selective conversions in water. The nucleophilic aromatic substitution reactions of 1,2,3-trichloro-4,6-dinitrobenzene (DNTCB), which are industrially important reactions, were studied as model reactions. The efficiency of cationic micellar solutions was ascribed to the cation-π interaction of surfactant’s cationic head group and substrate (DNTCB), which played significant role in solubilization of substrate in the micelles, and in activation of substrate for the nucleophilic substitution reactions. The study shows that the aqueous micellar solutions of cationic surfactants can be efficient and environmentally benign catalytic-solvent media for nucleophilic aromatic substitution reactions, which are conventionally carried out in organic solvents.

Efficiency of aqueous solutions of cationic surfactants in micellar catalysis of nucleophilic aromatic substitution reactions

ACS Spring Meeting 2021

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