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Wall-Coated Polymer Brushes as Support for Chiral Organocatalysts in Microreactors

Wall-Coated Polymer Brushes as Support for Chiral Organocatalysts in Microreactors Abstract Cinchona alkaloid and proline derivatives as enantioselective catalysts were covalently attached onto the inner walls of a microreactor using glycidyl methacrylate polymer brushes. The successful formation of the organocatalystfunctionalized brush layers on flat silicon oxide surfaces was confirmed by several techniques such as Fourier transform infrared (FT-IR), ellipsometry, and X-ray photoelectron spectroscopy (XPS). The applicability of the cinchona alkaloid (cinchonidine or quinidine)- and proline-containing polymer brushes in a microreactor was demonstrated for the Diels-Alder reaction between anthrone and N-substituted maleimides, and the aldol reaction between 4-nitrobenzaldehyde and cyclohexanone, respectively, which showed moderate conversions (up to 55% and 23%, respectively) and moderate to good enantioselectivities (up to 55% and 93%, respectively). The pristine catalytic activity of the microreactor was intact even after 1 month. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Flow Chemistry Springer Journals

Wall-Coated Polymer Brushes as Support for Chiral Organocatalysts in Microreactors

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References (44)

Publisher
Springer Journals
Copyright
2014 Akadémiai Kiadó
ISSN
2062-249X
eISSN
2063-0212
DOI
10.1556/jfc-d-14-00034
Publisher site
See Article on Publisher Site

Abstract

Abstract Cinchona alkaloid and proline derivatives as enantioselective catalysts were covalently attached onto the inner walls of a microreactor using glycidyl methacrylate polymer brushes. The successful formation of the organocatalystfunctionalized brush layers on flat silicon oxide surfaces was confirmed by several techniques such as Fourier transform infrared (FT-IR), ellipsometry, and X-ray photoelectron spectroscopy (XPS). The applicability of the cinchona alkaloid (cinchonidine or quinidine)- and proline-containing polymer brushes in a microreactor was demonstrated for the Diels-Alder reaction between anthrone and N-substituted maleimides, and the aldol reaction between 4-nitrobenzaldehyde and cyclohexanone, respectively, which showed moderate conversions (up to 55% and 23%, respectively) and moderate to good enantioselectivities (up to 55% and 93%, respectively). The pristine catalytic activity of the microreactor was intact even after 1 month.

Journal

Journal of Flow ChemistrySpringer Journals

Published: Jan 1, 2015

Keywords: chemistry/food science, general; green chemistry; organic chemistry; inorganic chemistry; nanochemistry; industrial chemistry/chemical engineering

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