Selective Aerobic Benzylic Alcohol Oxidation of Lignin Model Compounds: Route to Aryl Ketones

• Published in: ChemCatChem Vol. 7; no. 3; pp. 401 - 404
• Main Authors: Dawange, Monali, Galkin, Maxim V., Samec, Joseph S. M.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.02.2015; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: Alcohol; biomass valorization; heterogeneous catalysis; lignin; Oxidation; palladium
• ISSN: 1867-3880; 1867-3899; 1867-3899
• DOI: 10.1002/cctc.201402825

A mild and chemoselective oxidation of the α‐alcohol in β‐O‐4′‐ethanoaryl and β‐O‐4′‐glycerolaryl ethers has been developed. The benzylic alcohols were selectively dehydrogenated to the corresponding ketones in 60–93 % yield. A one‐pot selective route to aryl ethyl ketones was performed. The catalytic system comprises recyclable heterogeneous palladium, mild reaction conditions, green solvents, and oxygen in air as oxidant. Catalytic amounts of a coordinating polyol were found pivotal for an efficient aerobic oxidation. The ligninator: A mild and chemoselective oxidation of the α‐alcohol in β‐O‐4′ lignin model compounds is developed. The benzylic alcohols are selectively dehydrogenated to the corresponding ketones in 60–93 % yield. A one‐pot selective route to aryl ethyl ketones is performed. The catalytic system comprises recyclable heterogeneous palladium, mild reaction conditions, green solvents, and oxygen in air as oxidant.