Cerium(III) Chloride Catalyzed Michael Reaction of 1,3-Dicarbonyl Compounds and Enones in the Presence of Sodium Iodide Under Solvent-Free Conditions

✍ Scribed by Giuseppe Bartoli; Marcella Bosco; Maria Cristina Bellucci; Enrico Marcantoni; Letizia Sambri; Elisabetta Torregiani

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 189 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199903)1999:3<617::aid-ejoc617>3.0.co;2-r

✦ Synopsis

Cerium(III) chloride heptahydrate / Catalysis / 1,3-Dicarbonyl compounds / Enones / Michael reactions Cerium(III) chloride heptahydrate in the presence of sodium liquid at room temperature, the reaction can also be performed without solvents. The CeCl 3 • 7 H 2 O/NaI catalyst iodide catalyses the Michael addition of 1,3-dicarbonyl compounds to α,β-unsaturated ketones and α,β-unsaturated system can be easily separated from the reaction mixture and it can be reused without an appreciable loss of activity. aldehydes with extraordinary efficiency. The very mild conditions allow high chemoselectivity as shown by the Advantages of the present procedure, which utilizes cheap and "friendly" reagents, over the previously reported ones, absence of the typical side reactions, which can be observed in the conventional base-catalyzed processes. More are discussed. interestingly, when at least one of the starting materials is up procedure (filtration through a short column of silica gel