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Unusual deactivation in the asymmetric hydrogenation of itaconic acid

Research output: Journal contributions › Journal articles › Research › peer-review

Standard

Unusual deactivation in the asymmetric hydrogenation of itaconic acid. / Schmidt, Thomas; Baumann, Wolfgang; Drexler, Hans‐Joachim et al.
In: Journal of Organometallic Chemistry, Vol. 696, No. 9, 01.05.2011, p. 1760-1767.

Research output: Journal contributions › Journal articles › Research › peer-review

Harvard

Schmidt, T, Baumann, W, Drexler, HJ & Heller, D 2011, 'Unusual deactivation in the asymmetric hydrogenation of itaconic acid', Journal of Organometallic Chemistry, vol. 696, no. 9, pp. 1760-1767. https://doi.org/10.1016/j.jorganchem.2010.12.020

APA

Schmidt, T., Baumann, W., Drexler, HJ., & Heller, D. (2011). Unusual deactivation in the asymmetric hydrogenation of itaconic acid. Journal of Organometallic Chemistry, 696(9), 1760-1767. https://doi.org/10.1016/j.jorganchem.2010.12.020

Vancouver

Schmidt T, Baumann W, Drexler HJ, Heller D. Unusual deactivation in the asymmetric hydrogenation of itaconic acid. Journal of Organometallic Chemistry. 2011 May 1;696(9):1760-1767. doi: 10.1016/j.jorganchem.2010.12.020

Bibtex

@article{91b9b102ab5c4643a47fc669a9cf42c8,
title = "Unusual deactivation in the asymmetric hydrogenation of itaconic acid",
abstract = "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.",
keywords = "Chemistry, Homogeneous catalysis, Enantioselective hydrogenation, Itaconic acid, Catalyst deactivation, Rhodium alkyl complex",
author = "Thomas Schmidt and Wolfgang Baumann and Hans‐Joachim Drexler and Detlef Heller",
year = "2011",
month = may,
day = "1",
doi = "10.1016/j.jorganchem.2010.12.020",
language = "English",
volume = "696",
pages = "1760--1767",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
publisher = "Elsevier B.V.",
number = "9",

}

RIS

TY - JOUR

T1 - Unusual deactivation in the asymmetric hydrogenation of itaconic acid

AU - Schmidt, Thomas

AU - Baumann, Wolfgang

AU - Drexler, Hans‐Joachim

AU - Heller, Detlef

PY - 2011/5/1

Y1 - 2011/5/1

N2 - 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.

AB - 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.

KW - Chemistry

KW - Homogeneous catalysis

KW - Enantioselective hydrogenation

KW - Itaconic acid

KW - Catalyst deactivation

KW - Rhodium alkyl complex

UR - http://www.scopus.com/inward/record.url?scp=79954993724&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2010.12.020

DO - 10.1016/j.jorganchem.2010.12.020

M3 - Journal articles

VL - 696

SP - 1760

EP - 1767

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

IS - 9

ER -

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