Pd-C catalysed allylic oxidation using nitrobenzene as a hydrogen acceptor

02 September 2005

Hayashi and coworkers* have shown that secondary allylic alcohols can be oxidised to the corresponding enones using nitrobenzene as a hydrogen acceptor and catalytic palladium on carbon. The examples given are sugars and a steroid. Yields are very good. Obviously, nitrobenzene and its reaction byproduct (aniline) are not the most favoured species for the process chemist, but this protocol may nevertheless prove useful in certain circumstances.

*T. Tanaka, H. Kawabata and M. Hayashi, Tetrahedron Letters, 2005, 46, 4989-4991.