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Magnetically recoverable catalyst for the asymmetric Henry reaction based on a substituted imidazolidine-4-one copper(II) complex supported by Fe3O4 center dot SiO2 nanoparticles
Authors: Bhosale Dattatry | Drabina Pavel | Kincl Miloslav | Vlček Milan | Sedlák Miloš
Year: 2015
Type of publication: článek v odborném periodiku
Name of source: Tetrahedron Asymmetry
Publisher name: Elsevier Science BV
Place: Amsterdam
Page from-to: 1300-1306
Titles:
Language Name Abstract Keywords
cze Magneticky separovatelný katalyzátor pro asymetrickou Henryho reakci, založený na substituovaných měďnatých komplexech imidazolidin-4-onu vázaného na nanočástice Fe3O4 s SiO2 jádrem Byla popsána příprava a charakterizace heterogenních recyklovatelných katalyzátorů založených na Cu(II) komplexech magnetických nanočástic Fe3O4 s SiO2 jádrem a s (2R,5S)-5-isopropyl-5-methyl-2-(pyridin-2-y)imidazolidin-4-onem. Molekuly ligandu byly připojeny k povrchu koordinační vazbou. Katalyzátor byl charakterizován DLS, FT-IR, SEM a mikroanalýzou. Reakce subst. aldehydů s nitromethanem katalyzovaná tímto komplexem poskytuje vysoké výtěžky (82-99%) a vysokou enantioselektivitu (68-94%). Reakční rychlost klesá kvůli tvorbě agregátů částic katalyzátoru (115-834 nm) v závislosti na jejich koncentraci. Po 10-ti násobné recyklaci mírně klesá katalytická aktivita (o cca 10%) avšak enantioselektivita zůstává stejná (cca 94% ee). Katalyzátor byl testován při syntéze intermediátu léčiva medical drug (R)-Salmeterolu (výtěžek 72%; 91% ee). komplexy; nanočástice; adsorpce; separace; ligandy
eng Magnetically recoverable catalyst for the asymmetric Henry reaction based on a substituted imidazolidine-4-one copper(II) complex supported by Fe3O4 center dot SiO2 nanoparticles The preparation and characterization of a heterogeneous recyclable catalyst based on Cu(II) complex of magnetic nanoparticles Fe3O4 center dot SiO2 with (2R,5S)-5-isopropyl-5-methyl-2-(pyridine-2-y)imidazolidine-4-one is described. The ligand molecules were attached to the surface by means of coordination bonds. The catalyst was characterized using DLS, FT-IR spectroscopy, SEM, and microanalysis. The reaction of substituted aldehydes with nitromethane catalyzed with this complex proceeded with high yields (82-99%) and high enantioselectivity (68-94%). The reaction rate decreased due to the formation of aggregated forms of the catalyst nanoparticles whose size (115-834 nm) depends on their concentration in the reaction medium. After a tenfold recycling of the catalyst, the catalytic activity slightly decreased (similar to 10%); however, no change in enantioselectivity was observed (similar to 94% ee). The efficiency of the catalyst prepared was also verified in the preparation of an intermediate of synthesis of the medical drug (R)-Salmeterol (yield 72%; 91% ee). transition-metal-complexes; nanoparticles; adsorption; separation; nitrogen ligands

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