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

Autor: Roman Nickisch, Michael A. R. Meier, Solveig M. Gabrielsen
Jazyk: angličtina
Rok vydání: 2020
Předmět:
Zdroj: ChemistrySelect, 5 (38), 11915-11920
ISSN: 2365-6549
DOI: 10.5445/ir/1000125659
Popis: 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.
Databáze: OpenAIRE