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

Organic Letters
Aurélien DenichouxIlhyong Ryu

Abstract

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.

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Citations

Dec 18, 2010·Advanced Synthesis & Catalysis·Jason R ZbiegMichael J Krische
Aug 2, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Steven GiboulotWalter Baratta
May 30, 2012·Chemical Communications : Chem Comm·Yasushi OboraShintaro Hatanaka
Aug 31, 2012·Organic Letters·Takashi KuwaharaIlhyong Ryu

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