Na@SiO(2)-Mediated Addition of Organohalides to Carbonyl Compounds for the Formation of Alcohols and Epoxides

Alcohols and epoxides were generated by the addition of organohalides to carbonyl compounds in the presence of sodium metal impregnated with silica gel (Na@SiO(2)) in THF at 25 °C through a radical pathway. Under the same conditions, Schiff bases were also successfully converted to the corresponding amines. Furthermore, the reaction of aldehydes with α-haloesters or 4-(chloromethyl)-coumarin with the aid of Na@SiO(2) generated trans epoxides. An unprecedented mechanism is proposed for their formation. The advantages associated with these new reactions include: (1) products are obtained in good-to-excellent yields, (2) reactions are completed at room temperatures in a short period of time (<2.0 h), (3) it is unnecessary to perform the reactions under anhydrous conditions, and (4) the entire process requires only simple manipulations.