The ‘‘one-pot” homogeneous hydrogenation of -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
Isotopomeric diols by "one pot" Ru-catalyzed homogeneous hydrogenation of dicarboxylic acids / L. Rosi; M. Frediani; P. Frediani. - In: JOURNAL OF ORGANOMETALLIC CHEMISTRY. - ISSN 0022-328X. - STAMPA. - 695:(2010), pp. 1314-1322. [10.1016/j.jorganchem.2010.02.015]
Isotopomeric diols by "one pot" Ru-catalyzed homogeneous hydrogenation of dicarboxylic acids.
ROSI, LUCA;FREDIANI, MARCO;FREDIANI, PIERO
2010
Abstract
The ‘‘one-pot” homogeneous hydrogenation of -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 distributionFile | Dimensione | Formato | |
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