TCCA-Mediated Oxidative Deprotection of a Benzylamine

Benzyl-protected amines are mainly deprotected on scale using palladium-catalyzed hydrogenolysis. The present study evaluates a metal and hydrogen-free alternative based on the amine moiety oxidation to provide the corresponding imine via halogenation. It has been observed on a model substrate that inexpensive and nontoxic trichloroisocyanuric acid (TCCA) proved highly efficient as the oxidant before a simple base could readily deliver the desired imine to be hydrolyzed. A safety assessment of the process was further carried out and showed no specific alert regarding the chloramine intermediate formation.