The Highly Effective Hydrogenolysis-Based Debenzylation of Tetraacetyl-Dibenzyl-Hexaazaisowurtzitane (TADBIW) Using a Palladium/DOWEX Catalyst Having a Synergistic Effect

A Pd/resin catalyst system was prepared using a simple process and it exhibited excellent performance during the catalytic hydrogenolysis-based debenzylation of tetraacetyl-dibenzyl-hexaazaisowurtzitane (TADBIW) to 2,6,8,12-tetraacetyl-2,4,6,8,10,12-hexaazaisowurtzitane (TAIW). Employing this system, the palladium concentration could be reduced from 1% to 0.4% while improving the yield from 92% to 98% under mild reaction conditions. These outstanding results can be attributed to a synergistic effect between the palladium and the acidic resin. A possible reaction mechanism is proposed for the acid-assisted removal of N-benzyl from TADBIW in the presence of this catalyst.