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Novel Access to Known and Unknown Thiourea Catalyst via a Multicomponent‐Reaction Approach
Author(s) -
Nickisch Roman,
Gabrielsen Solveig M.,
Meier Michael A R.
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202003336
Subject(s) - trifluoromethyl , thiourea , chemistry , aryl , moiety , catalysis , sulfone , phosphine oxide , organocatalysis , organic chemistry , combinatorial chemistry , phosphine , polymer chemistry , enantioselective synthesis , alkyl
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, s uch 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.