HCl/DMF for enhanced chemoselectivity in catalytic hydrogenolysis reactions

✍ Scribed by Agata Ochocinska; Anna Siegbahn; Ulf Ellervik

• Book ID: 104098153
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 244 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.07.142

✦ Synopsis

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.