CuO Nanoparticle-Catalyzed C–N, C–O, and C–S Cross-Coupling Reactions: Scope and Mechanism

How nanoparticles can change the way we do catalytic reactions.

Science fiction writers have been hammering for a long time about how nanotechnology will change our world. Some of these novels are literally wonderful, with many technological marvels available only through the control of matter at the nanoscale. However, some of these nanotools are available today, and though less wonderful, they are probably more useful.

The group of Punniyamurthy (Indian Institute of Technology Guwahati, India) reports a broad scope study on the impact of CuO nanoparticles on C–X bond formation. More specifically, on the uses of these nanoparticles for the C–N, C–O, and C–S cross-coupling reactions. In a series of tables, they test the coupling of halobenzene derivatives, specially with iodine, and different nucleophiles including amides, imidazoles, indole and aniline, phenols and aliphatic alcohols and thiophenols. Different protocols are developed for each nucleophile with yields ranging from good to excellent. It seems that iodine is the best halogen for the transformation, but reactions are ligand-free, employing mainly KOH as the base, and the catalyst is easily recovered and reused. It sounds like a good alternative to conventional catalysts for some transformations.

J. Org. Chem., 2009, 74 (5), pp 1971–1976. See: 10.1021/jo8024253