Magnetic superbasic proton sponges are readily removed and permit direct product isolation
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Authors
Schneider, Elia M.
Hofer, Corinne J.
Zeltner, Martin
Stettler, Robert D.
Hess, Samuel C.
Grass, Robert N.
Stark, Wendelin J.
Author (Corporation)
Publication date
2014
Typ of student thesis
Course of study
Collections
Type
01A - Journal article
Editors
Editor (Corporation)
Supervisor
Parent work
The Journal of Organic Chemistry
Special issue
DOI of the original publication
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Series
Series number
Volume
79
Issue / Number
22
Pages / Duration
10908–10915
Patent number
Publisher / Publishing institution
American Chemical Society
Place of publication / Event location
Edition
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Abstract
Workup in organic synthesis can be very time-consuming, particularly when using reagents with both a solubility similar to that of the desired products and a tendency not to crystallize. In this respect, reactions involving organic bases would strongly benefit from a tremendously simplified separation process. Therefore, we synthesized a derivative of the superbasic proton sponge 1,8-bis(dimethylamino)naphthalene (DMAN) and covalently linked it to the strongest currently available nanomagnets based on carbon-coated cobalt metal nanoparticles. The immobilized magnetic superbase reagent was tested in Knoevenagel- and Claisen-Schmidt-type condensations and showed conversions of up to 99%. High yields of up to 97% isolated product could be obtained by simple recrystallization without using column chromatography. Recycling the catalyst was simple and fast with an insignificant decrease in catalytic activity.
Keywords
Catalysts, Chemical reactions, Condensation, Nanoparticles, Reagents
Subject (DDC)
500 - Naturwissenschaften und Mathematik
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ISBN
ISSN
0022-3263
1520-6904
1520-6904
Language
English
Created during FHNW affiliation
No
Strategic action fields FHNW
Publication status
Published
Review
Peer review of the complete publication
Open access category
Closed
License
Citation
SCHNEIDER, Elia M., Renzo RASO, Corinne J. HOFER, Martin ZELTNER, Robert D. STETTLER, Samuel C. HESS, Robert N. GRASS und Wendelin J. STARK, 2014. Magnetic superbasic proton sponges are readily removed and permit direct product isolation. The Journal of Organic Chemistry. 2014. Bd. 79, Nr. 22, S. 10908–10915. DOI 10.1021/jo501913z. Verfügbar unter: https://irf.fhnw.ch/handle/11654/47273