Isotopomeric diols by “one-pot” Ru-catalyzed homogeneous hydrogenation of dicarboxylic acids

The “one-pot” homogeneous hydrogenation of γ-butyrolactone and succinic or fumaric acid to 1,4-butandiol, have been successfully realized in the presence of the catalytic system [Ru(acac)3]/triphos] [triphos:MeC(CH2PPh2)3]. The influence of some reaction parameters on the regioselectivity and the rate of the reaction were investigated. The study was then extended to the “one-pot” synthesis of isotopomeric 1,4-butandiols by deuteration of the appropriate substrates in a deuterated solvent. 1,4-butandiol-d8, which was fully characterized, was obtained with 96% yield and 100% isotopomeric selectivity. A mechanism was proposed to rationalize the role of catalyst, solvent and deuterium distribution.

Graphical abstractHydrogenation of 1,4-dicarboxylic acids gives 1,4-butandiol using a ruthenium catalyst, triphos ligand and methanol. The one pot synthesis of isotopomeric butandiols containing 6, 8 or 10 deuterium atoms was easily achieved with this catalytic system.Figure optionsDownload full-size imageDownload as PowerPoint slide