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

The one-pot homogeneous hydrogenation of gamma-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-d(8), 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. (C) 2010 Elsevier B.V. All rights reserved.