Synthesis of 2-hydroxymethyl ketones by ruthenium hydride-catalyzed cross-coupling reaction of alpha,beta-unsaturated aldehydes with primary alcohols.
The cross-coupling reaction of alpha,beta-unsaturated aldehydes with primary alcohols to give 2-hydroxymethyl ketones was achieved using RuHCl(CO)(PPh(3))(3) as a catalyst. This atom-economical reaction is likely to proceed via the hydroruthenation of alpha,beta-unsaturated aldehydes followed by an aldol reaction of the resultant enolates with aldehydes to give alpha-formylated ketones, which undergo transfer hydrogenation with primary alcohols leading to alpha-hydroxymethyl ketones. The reduction step can generate aldehydes, participating in the next catalytic cycle.
Denichoux
Aurélien
A
Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan.
Fukuyama
Takahide
T
Doi
Takashi
T
Horiguchi
Jiro
J
Ryu
Ilhyong
I