Decarboxylative synthesis of α-iodoalkylammonium salts via ammonio oxime esters

Abstract α-Iodomethylammonium salts have recently garnered significant attention in drug discovery and materials science. However, the synthesis of their α-alkyl-substituted derivatives remains challenging in classical nucleophilic substitution reactions between tertiary amines and 1,1-diiodoalkanes due to steric hindrance. To address this limitation, we developed a radical-based synthetic approach that fundamentally differs from traditional nucleophilic substitution strategies. This method utilizes ammonio oxime esters as novel precursors of α-ammonio radicals, enabling the synthesis of a broad range of α-iodoalkylammonium salts.