Chemoselective control of hydrogenation among aromatic carbonyl and benzyl alcohol derivatives using Pd/C(en) catalyst

• Published in: Tetrahedron Vol. 57; no. 23; pp. 4817 - 4824
• Main Authors: Hattori, Kazuyuki, Sajiki, Hironao, Hirota, Kosaku
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 04.06.2001; Elsevier
• Subjects: 10% Pd/C(en); aromatic carbonyl; Chemistry; Chemistry, Organic; deacetoxylation; heterogeneous catalysis; Physical Sciences; Science & Technology; selective hydrogenation; 10% Pd/C(en); aromatic carbonyl; deacetoxylation; heterogeneous catalysis; selective hydrogenation; KETONES; ASYMMETRIC TRANSFER HYDROGENATION; HYDROGENOLYSIS; LIGANDS; RETENTION; COMPLEXES; ALDEHYDES
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/S0040-4020(01)00421-5

The hydrogenolysis of aromatic ketones and aldehydes quite smoothly give the corresponding methylene compounds via the formation of the intermediary benzyl alcohols in the presence of Pd/C as a catalyst. Therefore, it is extremely difficult to isolate the intermediary benzyl alcohol selectively. This paper describes a mild and chemoselective hydrogenation method of an aromatic carbonyl compound to benzyl alcohol using the 10% Pd/C(en) catalyst and its application to the chemoselective deacetoxylation reaction at the benzylic position in the presence of the benzyl alcohol functionality within the molecule. Graphic