Unusual deactivation in the asymmetric hydrogenation of itaconic acid

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The formation of unusual Rh(III) substrate complexes from [Rh(DIPAMP)(MeOH)2]BF4 and itaconic acid has been detected which leads to the deactivation of the catalyst. The influence of different parameters on the formation of such complexes, namely substrate concentration, reaction time, temperature, acidic and basic additives, was investigated with different NMR methods. Two different Rh(III) substrate complexes are formed whose ratio is strongly dependent on substrate concentration and reaction time. The pH value of the solution shows a strong influence on the chemical shifts of the 31P NMR signals of such complexes. A catalyst-mediated esterification of itaconic acid in methanol was detected. Extended investigations provide detailed 1H, 13C and 31P NMR data for the Rh(III) complexes and information about their stability in solution.
Original languageEnglish
JournalJournal of Organometallic Chemistry
Volume696
Issue number9
Pages (from-to)1760-1767
Number of pages8
ISSN0022-328X
DOIs
Publication statusPublished - 01.05.2011

    Research areas

  • Chemistry - Homogeneous catalysis, Enantioselective hydrogenation, Itaconic acid, Catalyst deactivation, Rhodium alkyl complex

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