Na@SiO₂-Mediated Addition of Organohalides to Carbonyl Compounds for the Formation of Alcohols and Epoxides.

ABSTRACT: Alcohols and epoxides were generated by the addition of organohalides to carbonyl compounds in the presence of sodium metal impregnated with silica gel (Na@SiO₂) 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@SiO₂ 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,

SUBMITTER: Kapoor M 

PROVIDER: S-EPMC5113255 | biostudies-literature | 2016 Nov

REPOSITORIES: biostudies-literature