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Selective Debenzylation of Benzyl Protected Groups with SiliaCat Pd(0) under Mild Conditions

Protection of functional groups such as alcohols, acids, and amines in the manufacture of pharmaceuticals and fine chemicals is often necessary to avoid possible side reactions during the typical multi-step syntheses of complex organic molecules carried out by these industries. Formation of benzyl esters and ethers (O-protection) is a commonly used protection method in numerous drugs syntheses, as the Bn protecting group features ease of preparation and chemical stability toward a number of reaction conditions. Selective and smooth deprotection is critical, and the commonly used method makes use of catalytic hydrogenolysis of protecting benzylic groups with H2 under pressure in the presence of a heterogeneous Pd/C catalyst or Raney Ni. Often, however, the deprotection reaction conditions are not compatible with other functional groups, such as nitro, unsaturated bonds, and halogen groups. For example, the state of the art Pd/C catalyst for the O-debenzylation of benzyl protected alcohols and acids makes use of the following recommended reaction conditions: