TY - JOUR
T1 - Wall-Coated Polymer Brushes as Support for Chiral Organocatalysts in Microreactors
AU - Munirathinam, Rajesh
AU - Leoncini, Andrea
AU - Huskens, Jurriaan
AU - Wormeester, Herbert
AU - Verboom, Willem
PY - 2015
Y1 - 2015
N2 - 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.
AB - 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.
KW - 2023 OA procedure
U2 - 10.1556/JFC-D-14-00034
DO - 10.1556/JFC-D-14-00034
M3 - Article
SN - 2062-249X
VL - 5
SP - 37
EP - 42
JO - Journal of flow chemistry
JF - Journal of flow chemistry
IS - 1
ER -