Reactivity Profile
Organocerium reagents prepared from cerium triiodide and organolithiums have reduced basicity and possess enhanced nucleophilicity toward the carbonyl group; promotes aldol reaction between α-halo ketones and aldehydes; in combination with LiAlH4 is a selective 1,2-reducing agent.
Synthesis
Pure CeI3 (Cerium (III) iodide) is prepared by reacting metallic cerium with iodine or mercury(II) iodide at high temperature.Another method is to dissolve CeO2 in an aqueous HI solution, adding 12 moles of NH4I per mole of CeO2 and evaporating the mixture to dryness. The mixture is heated in vacuo at 300- 350 °C to leave pure CeI3. CeI3 is prepared in situ by reacting powdered cerium with iodine in THF[1-4].
References
1. Jantsch, G.; Grubitsch, H.; Hoffmann, F.; Alber, H. ZC 1929, 185, 49.
2. Asprey, L. B.; Keenan, T. K.; Kruse, F. H. IC 1964, 3, 1137.
3. Taylor, M. D. CRV 1962, 62, 503.
4. Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. JOC 1984, 49, 3904.