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Dynamic Covalent Chemistry of Aldehyde Enamines: Bi-III- and Sc-III-Catalysis of Amine-Enamine Exchange
KTH, School of Chemical Science and Engineering (CHE), Chemical Engineering and Technology, Energy Processes.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2017 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 23, no 49, 11908-11912 p.Article in journal (Refereed) Published
Abstract [en]

The dynamic exchange of enamines from secondary amines and enolizable aldehydes has been demonstrated in organic solvents. The enamine exchange with amines was efficiently catalyzed by Bi(OTf)(3) and Sc(OTf)(3) (2mol%) and the equilibria (60mm) could be attained within hours at room temperature. The formed dynamic covalent systems displayed high stabilities in basic environment with <2% by-product formation within one week after complete equilibration. This study expands the scope of dynamic C-N bonds from imine chemistry to enamines, enabling further dynamic methodologies in exploration of this important class of structures in systems chemistry.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2017. Vol. 23, no 49, 11908-11912 p.
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-214483DOI: 10.1002/chem.201702363ISI: 000408834700026Scopus ID: 2-s2.0-85028591683OAI: oai:DiVA.org:kth-214483DiVA: diva2:1148313
Note

QC 20171010

Available from: 2017-10-10 Created: 2017-10-10 Last updated: 2017-10-10Bibliographically approved

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Zhang, YangXie, ShengRamström, Olof

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