HCl/DMF for enhanced chemoselectivity in catalytic hydrogenolysis reactions

An improved, chemoselective hydrogenolysis method has been developed. By employing a solvent-acid combination (i.e., DMF–aq HCl) we were able to favor debenzylation rather than aromatic hydrogenation and acid-mediated bond cleavage which are the two main drawbacks of these reactions. The generality of the method, which was primarily developed as a solution to a carbohydrate problem, is shown by the successful hydrogenolysis of 1,8-naphthalide, a previously unsolved problem.