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Novel Access to Known and Unknown Thiourea Catalyst via a Multicomponent-Reaction Approach

Nickisch, Roman; Gabrielsen, Solveig M.; Meier, Michael A. R.

Abstract:
Thioureas are frequently used in organocatalysis and typically rely on 3,5‐bis(trifluoromethyl) phenyl moieties motifs to enhance their catalytic activity. In this work, these common motifs were replaced with tailorable functional groups, such as ester or sulfone aryls, applying elemental sulfur in a multicomponent reaction (MCR) strategy for the first time for thiourea catalyst synthesis. First, several thioureas bearing aryl, benzylic or aliphatic moieties were synthesized and tested for their hydrogen bonding strength by evaluating thiourea phosphine oxide complexes via $^{31}$P NMR and their catalytic activity in an Ugi four‐component reaction (U‐4CR). Finally, ester and sulfone aryl thioureas were tested in the aminolysis of propylene carbonate, leading to conversions similar to those previously reported in the literature using the 3,5‐bis(trifluoromethyl)phenyl moiety, proving that these groups are suitable alternatives for the trifluoromethyl group.

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Verlagsausgabe §
DOI: 10.5445/IR/1000125659
Veröffentlicht am 05.11.2020
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Institut für Biologische und Chemische Systeme (IBCS)
Publikationstyp Zeitschriftenaufsatz
Publikationsdatum 15.10.2020
Sprache Englisch
Identifikator ISSN: 2365-6549
KITopen-ID: 1000125659
HGF-Programm 47.01.01 (POF III, LK 01)
Biol.Netzwerke u.Synth.Regulat. ITG+ITC
Erschienen in ChemistrySelect
Band 5
Heft 38
Seiten 11915-11920
Vorab online veröffentlicht am 13.10.2020
Nachgewiesen in Scopus
Web of Science
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