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Ion-tagged prolinamide organocatalysts for the direct aldol reaction on-water

Eyckens, Daniel J., Brozinski, Hannah L., Delaney, Joshua P., Servinis, Linden, Naghashian, Sahar and Henderson, Luke C. 2016, Ion-tagged prolinamide organocatalysts for the direct aldol reaction on-water, Catalysis letters, vol. 146, no. 1, pp. 212-219, doi: 10.1007/s10562-015-1630-4.

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Title Ion-tagged prolinamide organocatalysts for the direct aldol reaction on-water
Author(s) Eyckens, Daniel J.
Brozinski, Hannah L.
Delaney, Joshua P.
Servinis, Linden
Naghashian, Sahar
Henderson, Luke C.ORCID iD for Henderson, Luke C. orcid.org/0000-0002-4244-2056
Journal name Catalysis letters
Volume number 146
Issue number 1
Start page 212
End page 219
Total pages 8
Publisher Springer
Place of publication Berlin, Germany
Publication date 2016-01
ISSN 1011-372X
1572-879X
Keyword(s) Science & Technology
Physical Sciences
Chemistry, Physical
Chemistry
Organocatalyst
Imidazolium
Aldol
Onwater
HIGHLY EFFICIENT ORGANOCATALYSTS
ASYMMETRIC MICHAEL REACTIONS
AQUEOUS-MEDIA
BIFUNCTIONAL ORGANOCATALYSTS
RECOVERABLE ORGANOCATALYSTS
ADDITION-REACTIONS
LIQUID
CATALYSIS
KETONES
NITROSTYRENES
Summary A concise synthesis of two imidazolium ion-tagged prolinamide organocatalysts 3 and 4, varying in anionic component (CF3COO- and PF6 -, respectively) is presented. The latter could be classified as an ionic liquid with a melting point of 66.3 °C, and glass transition temperature of 14.5 °C. The efficiency of each catalyst was compared via a direct aldol reaction revealing a large contrast in catalytic performance, with the catalyst bearing the PF6 - anion being superior. The optimal conditions were determined to be an on-water reaction system, and substrate scoping gave a range of desired aldol products in high conversion (up to >99 %), dr (up to 98:2), and er (up to 96:4). The application of these catalysts to beta-nitrostyrene conjugate addition is also presented. Graphical Abstract: [Figure not available: see fulltext.]
Language eng
DOI 10.1007/s10562-015-1630-4
Field of Research 030503 Organic Chemical Synthesis
030601 Catalysis and Mechanisms of Reactions
030504 Organic Green Chemistry
0306 Physical Chemistry (Incl. Structural)
0904 Chemical Engineering
Socio Economic Objective 970103 Expanding Knowledge in the Chemical Sciences
HERDC Research category C1 Refereed article in a scholarly journal
ERA Research output type C Journal article
Copyright notice ©2016, Springer
Persistent URL http://hdl.handle.net/10536/DRO/DU:30083336

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