Combination of a Suzuki cross-coupling reaction using a water-soluble palladium catalyst with an asymmetric enzymatic reduction towards a one-pot process in aqueous medium at room temperature

Beitrag in einer Fachzeitschrift
(Originalarbeit)


Details zur Publikation

Autor(en): Borchert S, Burda E, Schatz J, Hummel W, Gröger H
Zeitschrift: Journal of Molecular Catalysis B-Enzymatic
Verlag: Elsevier
Jahr der Veröffentlichung: 2012
Band: 84
Seitenbereich: 89-93
ISSN: 1381-1177


Abstract


We report the combination of a palladium-catalyzed Suzuki cross-coupling reaction with an enzymatic reduction in a one-pot process in aqueous medium, in which both reaction steps are conducted at room temperature. By using a water-soluble palladium catalyst system, which is prepared from commercially available palladium chloride and TPPTS (tris(3-sulfonatophenyl)phosphine hydrate, sodium salt), the palladium-catalyzed step runs at room temperature in a mixture of isopropanol and water. After adjusting the pH value to pH 7, the resulting biaryl ketone is then directly reduced in situ via an enzymatic asymmetric reduction in the presence of an alcohol dehydrogenase (ADH), leading to the desired alcohol with up to >95% conversion (over two steps) and excellent enantioselectivities of >99% ee. Notably, both enantiomers of the desired alcohol are accessible depending on the source of applied ADH. © 2012 Elsevier B.V. All rights reserved.



FAU-Autoren / FAU-Herausgeber

Borchert, Sonja
Professur für Organische Chemie
Schatz, Jürgen Prof. Dr.
Professur für Organische Chemie


Autor(en) der externen Einrichtung(en)
Heinrich-Heine-Universität Düsseldorf


Zitierweisen

APA:
Borchert, S., Burda, E., Schatz, J., Hummel, W., & Gröger, H. (2012). Combination of a Suzuki cross-coupling reaction using a water-soluble palladium catalyst with an asymmetric enzymatic reduction towards a one-pot process in aqueous medium at room temperature. Journal of Molecular Catalysis B-Enzymatic, 84, 89-93. https://dx.doi.org/10.1016/j.molcatb.2012.03.006

MLA:
Borchert, Sonja, et al. "Combination of a Suzuki cross-coupling reaction using a water-soluble palladium catalyst with an asymmetric enzymatic reduction towards a one-pot process in aqueous medium at room temperature." Journal of Molecular Catalysis B-Enzymatic 84 (2012): 89-93.

BibTeX: 

Zuletzt aktualisiert 2019-10-04 um 21:50