Sustainable flow Oppenauer oxidation of secondary benzylic alcohols with a heterogeneous zirconia catalyst

Sustainable flow Oppenauer oxidation of secondary benzylic alcohols with a heterogeneous zirconia catalyst 

Rajeev Chorghade †, Claudio Battilocchio †, Joel M. Hawkins ‡, and Steven V. Ley *†

Innovative Technology Centre, Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, Cambridge, U.K., and Pfizer Worldwide Research and Development, Eastern Point Road, Groton, Connecticut 06340, United States

Org. Lett., 2013, 15 (22), pp 5698–5701

DOI: 10.1021/ol4027107

http://pubs.acs.org/doi/abs/10.1021/ol4027107

A flow chemistry process for the Oppenauer oxidation of benzylic secondary alcohols using partially hydrated zirconium oxide and a simple carbonyl containing oxidant such as acetone, cyclohexanone, and neopentanal is reported. The heterogeneous oxidative system could be applied to a wide range of functionalized alcohol substrates, allowing clean and fast delivery of ketone products within a few minutes between 40 and 100 °C.