Palladium-Catalyzed Carbonation–Diketonization of Terminal Aromatic Alkenes via Carbon–Nitrogen Bond Cleavage for the Synthesis of 1,2-Diketones

Nitroalkanes and styrenes as raw materials for the preparation of diketones.

What attracted my eye in this case was the “1,2-Diketones” in the title, since these products are valuable starting materials for the preparation of many heterocycles. Jiang et al. (South China University of Technology, China) show in this paper a protocol for the generation of these ketones using styrenes, nitroalkanes and Palladium. Maybe not the most useful protocol when you think on how many styrenes you can find in catalogs, but it can be useful when the time comes. 15 examples are given, with yields ranging from good to very good. One problem of the protocol is that you need to use AIBN and O2, so scaling up is gonna be… interesting.

J. Org. Chem., 2011, 76 (16), pp 6958–6961. See: 10.1021/jo201029p