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.
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.
Esaki
Hiroyoshi
H
Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, 5-6-1 Mitahora-higashi, Gifu 502-8585, Japan.
Ohtaki
Rumi
R
Maegawa
Tomohiro
T
Monguchi
Yasunari
Y
Sajiki
Hironao
H
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
D000438:Alcohols; D007659:Ketones; D010165:Palladium; D002244:Carbon