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

Rajesh Munirathinam, Andrea Leoncini, Jurriaan Huskens, Herbert Wormeester, Willem Verboom

Research output: Contribution to journalArticleAcademicpeer-review

2 Citations (Scopus)

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 organocatalyst-functionalized 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.
Original languageEnglish
Pages (from-to)37-42
Number of pages6
JournalJournal of flow chemistry
Volume5
Issue number1
DOIs
Publication statusPublished - 2015

Keywords

  • METIS-310915
  • IR-96725

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