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, and (4) the entire process requires only simple manipulations.

Review of Characteristics and Properties of Fe2o3/Sio2 as Water Pollution Prevention

“…The employment of colloid as support additionally will increase each substrate's effective extent and ambit and, therefore, the metal within the pores to decrease the activation entropy for negatron transfer. Isomers with internal steric resistance can modify additional thermodynamically stable conformers [67]. It was stated that Me2-CA-BTP/SiO2-P showed efficient adsorption selectivity towards 241Am(III) above 152Eu(III) in a wide range of nitric acid and acceptable adsorption kinetics work for adequate stability against irradiation in HNO3 solution.…”

Silica Gel Stabilized Na and Na/K Alloys: Highly Effective, Versatile and Environmentally Friendly Reducing Agents

“…In 2016, Na-SG(I) was employed by Hwu et al to mediate the addition of organohalides to carbonyl compounds, thus disclosing an alternative and original approach to the classical synthesis of alcohols involving, e.g., Grignard or organolithium reagents. 28 Indeed, Na-SG(I) promoted the reaction of aromatic, aliphatic, and allylic halides with a variety of aliphatic and aromatic aldehydes, ketones, and Schiff bases leading, under one-pot optimized reaction conditions [Na-SG(I) (1.3-2.0 equiv), halide (1.2 equiv), 1.0-3.0 h], to the formation of a variety of alcohols with good to very good overall yields (Scheme 10).…”