An Anion-Switchable Dual-Function Rotaxane Catalyst

In situ switching of the associated anions of a rotaxane catalyst between Cl- and TFPB- exposes its dialkylammonium and imidazolium stations, respectively, thereby selectively catalyzing the reactions of a mixture of trans-cinnamaldehyde and an aliphatic thiol to yield the Michael adduct and the thi...

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Published inAngewandte Chemie International Edition Vol. 62; no. 43; p. e202309889
Main Authors Tseng, I-Cheng, Zhang, Min-Xuan, Kang, Shih-Lun, Chiu, Sheng-Hsien
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 23.10.2023
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Anions
Catalysts
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Cinnamaldehyde
Physical Sciences
Rotaxanes
Science & Technology
FLUORESCENT
Anion Control
Rotaxanes
Thioacetalation
Michael Addition
Catalysis
MECHANICALLY INTERLOCKED MOLECULES
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Summary:In situ switching of the associated anions of a rotaxane catalyst between Cl- and TFPB- exposes its dialkylammonium and imidazolium stations, respectively, thereby selectively catalyzing the reactions of a mixture of trans-cinnamaldehyde and an aliphatic thiol to yield the Michael adduct and the thioacetal product, respectively. An anion-controllable rotaxane catalyst has been generated that can selectively catalyze the reaction between trans-cinnamaldehyde and an aliphatic thiol. The reaction occurs through either a Michael addition or thioacetalation pathway by exposing its dibenzylammonium or imidazolium station, respectively, to the reactants in its two switchable states.image
Bibliography:ObjectType-Article-1
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202309889