title: Novel Pd/C-catalyzed redox reactions between aliphatic secondary alcohols and ketones under hydrogenation conditions: application to H-D exchange reaction and the mechanistic study.
abstract: A liquid-phase redox system between secondary alcohols and ketones is described. Deuteration of either secondary alcohols or ketones using the Pd/C-H2-D2O system gave a mixture of deuterium-labeled secondary alcohols and ketones. The results indicated that the secondary alcohol was oxidized to the corresponding ketone without oxidants under the hydrogenation conditions and the hydrogenation of the aliphatic ketone to the corresponding secondary alcohol simultaneously proceeded. Detailed mechanistic studies on the redox system as well as the H-D exchange reaction are discussed.
authors.affiliation: Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, 5-6-1 Mitahora-higashi, Gifu 502-8585, Japan.
authors.forename: Hiroyoshi
authors.initials: H
authors.lastname: Esaki
authors.forename: Rumi
authors.initials: R
authors.lastname: Ohtaki
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Maegawa
authors.forename: Yasunari
authors.initials: Y
authors.lastname: Monguchi
authors.forename: Hironao
authors.initials: H
authors.lastname: Sajiki
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D041961:Deuterium Exchange Measurement; D006865:Hydrogenation; D007659:Ketones / Q000737:chemistry*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry
chemical_list: D000438:Alcohols; D007659:Ketones; D010165:Palladium; D002244:Carbon