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Recyclable Enantioselective Catalysts Based on Copper(II) Complexes of 2-(Pyridine-2-yl)imidazolidine-4-thione: Their Application in Asymmetric Henry Reactions
Authors: Nováková Gabriela | Drabina Pavel | Frumarová Božena | Sedlák Miloš
Year: 2016
Type of publication: článek v odborném periodiku
Name of source: Advanced synthesis and catalysis
Publisher name: Wiley-VCH
Place: Weinheim
Page from-to: 2541-2552
Titles:
Language Name Abstract Keywords
cze Recyklovatelné enantioselektivní katalyzátory založené na Cu(II) komplexech 2-(pyridin-2-yl)imidazolidin-4-thionu: Jejich užití při asymetrických Henryho reakcích Článek popisuje přípravu enantioselektivních katalyzátorů založených na derivátech imidazolidin-4-thionu a jejich následné zakotvení skrze atom síry na polymerní nosič. Nejprve jsme ověřili katalytickou aktivitu a enantioselektivitu při Henryho reakci homogenní varianty katalyzátoru, tj., samotné Cu(II) komplexy 2-(pyridin-2-yl)imidazolidin-4-thionu a 4-benzylsufanyl-2-(pyridin-2-yl)imidazolinu. Bylo zjištěno, že tyto katalyzátory vykazují vysokou enantioselektivitu (až 98% ee). Následně byl imidazolidin-4-thionový katalyzátor imobilizován na polymerní nosič na bázi kopolymeru styrenu a 4-vinylbenzyl chloridu. Tyto heterogenní katalyzátory byly rovněž testovány na jejich katalytickou aktivitu a enantioselektivitu při Henryho reakci. Bylo zjištěno, že všechny imobilizované katalyzátory jsou vysoce enantioselektivní (až 97% ee). Jejich recyklovatelnost byla testována na Henryho reakci 2-methoxybenzaldehydu s nitromethanem a bylo zjištěno, že ji lze opakovat desetkrát beze ztráty enantioselektivity. Recyklace; enantioselektivita; katalýza; Cu(II) komplexy; 2-pyridin-2-ylimidazolidin-4-thion; Henryho reakce
eng Recyclable Enantioselective Catalysts Based on Copper(II) Complexes of 2-(Pyridine-2-yl)imidazolidine-4-thione: Their Application in Asymmetric Henry Reactions This paper describes the preparation of enantioselective catalysts based on derivatives of imidazolidine-4-thione and their subsequent anchoring by means of a sulfur atom on a polymeric carrier. First, we verified the catalytic activity and enantioselectivity in the Henry reaction of the homogeneous variants of the catalysts, i.e., the copper(II) complexes of 2-(pyridine-2-yl)imidazolidine-4-thiones and 4-benzylsufanyl-2-(pyridine-2-yl)imidazolines themselves. It was found that these catalysts exhibit high enantioselectivity (up to 98% ee). Subsequently, the imidazolidine-4-thione catalysts were immobilized by anchoring to polymeric carriers based on a copolymer of styrene and 4-vinylbenzyl chloride. These heterogeneous catalysts were analogously tested with regard to their catalytic activity and enantioselectivity in the Henry reaction, and more-over, the possibility of their separation and reuse was studied. It was found that all the prepared immobilized catalysts are highly enantioselective (up to 97% ee). Their recycling ability was tested in Henry reaction of 2-methoxybenzaldehyde with nitromethane. It was found that they can be recycled more than ten times without any decrease of their enantioselectivity. Therefore, they present a better means of catalysis than the original copper(II) complexes of imidazolidine-4-ones from both economic as well as ecological points of view. Thus, such immobilized catalysts exhibit high application potential for the asymmetric Henry reaction. asymmetric catalysis; enantioselectivity; heterogeneous catalysis; immobilization; supported catalysts

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