Nano‐Aluminum Powder Mediated Allylation of Carbonyl Compounds in Aqueous Media

Abstract

A new and effective Barbier-Grignard allylation of aldehydes or ketones has been carried out with nano-aluminum powder in aqueous 0.1 mol•L -1 NH 4 Cl (aq.) under an atmosphere of nitrogen. Aromatic carbonyl compounds gave homoallylic alcohols in good yields. The effectiveness of reaction was strongly influenced by the steric environment surrounding the carbonyl group. Aliphatic carbonyl compounds proceeded in low yields. The dominant stereoisomer was an erythro-isomer when an ortho-hydroxyl carbonyl compound was reacted under such a reaction condition.

Zn-mediated electrochemical α-alkylation of amines with halogenated alkanes through convergent paired electrolysis

“…The Barbier–Grignard-type reaction is one of the most important methods for forming carbon–carbon bonds and is widely applied in modern organic synthetic chemistry. 1 Since Barbier's initial report of the reaction in 1899, a variety of metals, including zinc, 2 magnesium, 3 samarium, 4 aluminium, 5 indium, 6 cadmium, 7 antimony, 8 lead, 9 tin, 10 bismuth, 11 and manganese 12 have been applied in it. Among them, zinc, a relatively cheap and low-toxicity material, has been demonstrated to be an effective mediator of the Barbier–Grignard-type reaction and widely applied in industry.…”