Synthesis of 2-hydroxymethyl ketones by ruthenium hydride-catalyzed cross-coupling reaction of α,β-unsaturated aldehydes with primary alcohols

Aurélien Denichoux, Takahide Fukuyama, Takashi Doi, Jiro Horiguchi, Ilhyong Ryu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

"Chemical Equation Presented" The cross-coupling reaction of α,β-unsaturated aldehydes with primary alcohols to give 2-hydroxymethyl ketones was achieved using RuHCl(CO)(PPh3)3 as a catalyst. This atom-economical reaction is likely to proceed via the hydroruthenation of α,β-unsaturated aldehydes followed by an aldol reaction of the resultant enolates with aldehydes to give r-formylated ketones, which undergo transfer hydrogenation with primary alcohols leading to α-hydroxymethyl ketones. The reduction step can generate aldehydes, participating in the next catalytic cycle.

Original languageEnglish
Pages (from-to)1-3
Number of pages3
JournalOrganic Letters
Volume12
Issue number1
DOIs
StatePublished - 1 Jan 2010

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