4.7 Article

Guerbet reaction of primary alcohols leading to β-alkylated dimer alcohols catalyzed by iridium complexes

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 21, Pages 8306-8308

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo061400t

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[IrCl(cod)](2) and [Cp*IrCl2](2) complexes catalyzed efficiently the Guerbet reaction of primary alcohols to beta-alkylated dimer alcohols in good yields. For instance, the reaction of 1-butanol in the presence of [ Cp*IrCl2](2) (1 mol %), t-BuOK (40 mol %), and 1,7-octadiene (10 mol %) produced 2-ethyl1- hexanol in 93% yield. Various primary alcohols undergo the Guerbet reaction under the influence of Ir complexes to give the corresponding dimer alcohols in good yields. This method provides an alternative direct route to beta-alkylated primary alcohols which are prepared by aldol condensation of aldehydes followed by hydrogenation.

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