Dynamic Covalent Chemistry of Aldehyde Enamines: Bi(III)‐ and Sc(III)‐Catalysis of Amine–Enamine Exchange

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) (2 mol %) and the equilibria (60 mm) could be attained within hours at room temperature....

Descripción completa

Detalles Bibliográficos
Autores principales: Zhang, Yang, Xie, Sheng, Yan, Mingdi, Ramström, Olof
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5656824/
https://www.ncbi.nlm.nih.gov/pubmed/28722305
http://dx.doi.org/10.1002/chem.201702363
_version_ 1783273772852183040
author Zhang, Yang
Xie, Sheng
Yan, Mingdi
Ramström, Olof
author_facet Zhang, Yang
Xie, Sheng
Yan, Mingdi
Ramström, Olof
author_sort Zhang, Yang
collection PubMed
description 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) (2 mol %) and the equilibria (60 mm) 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.
format Online
Article
Text
id pubmed-5656824
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-56568242017-11-01 Dynamic Covalent Chemistry of Aldehyde Enamines: Bi(III)‐ and Sc(III)‐Catalysis of Amine–Enamine Exchange Zhang, Yang Xie, Sheng Yan, Mingdi Ramström, Olof Chemistry Full Papers 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) (2 mol %) and the equilibria (60 mm) 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. John Wiley and Sons Inc. 2017-08-09 2017-09-04 /pmc/articles/PMC5656824/ /pubmed/28722305 http://dx.doi.org/10.1002/chem.201702363 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Full Papers
Zhang, Yang
Xie, Sheng
Yan, Mingdi
Ramström, Olof
Dynamic Covalent Chemistry of Aldehyde Enamines: Bi(III)‐ and Sc(III)‐Catalysis of Amine–Enamine Exchange
title Dynamic Covalent Chemistry of Aldehyde Enamines: Bi(III)‐ and Sc(III)‐Catalysis of Amine–Enamine Exchange
title_full Dynamic Covalent Chemistry of Aldehyde Enamines: Bi(III)‐ and Sc(III)‐Catalysis of Amine–Enamine Exchange
title_fullStr Dynamic Covalent Chemistry of Aldehyde Enamines: Bi(III)‐ and Sc(III)‐Catalysis of Amine–Enamine Exchange
title_full_unstemmed Dynamic Covalent Chemistry of Aldehyde Enamines: Bi(III)‐ and Sc(III)‐Catalysis of Amine–Enamine Exchange
title_short Dynamic Covalent Chemistry of Aldehyde Enamines: Bi(III)‐ and Sc(III)‐Catalysis of Amine–Enamine Exchange
title_sort dynamic covalent chemistry of aldehyde enamines: bi(iii)‐ and sc(iii)‐catalysis of amine–enamine exchange
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5656824/
https://www.ncbi.nlm.nih.gov/pubmed/28722305
http://dx.doi.org/10.1002/chem.201702363
work_keys_str_mv AT zhangyang dynamiccovalentchemistryofaldehydeenaminesbiiiiandsciiicatalysisofamineenamineexchange
AT xiesheng dynamiccovalentchemistryofaldehydeenaminesbiiiiandsciiicatalysisofamineenamineexchange
AT yanmingdi dynamiccovalentchemistryofaldehydeenaminesbiiiiandsciiicatalysisofamineenamineexchange
AT ramstromolof dynamiccovalentchemistryofaldehydeenaminesbiiiiandsciiicatalysisofamineenamineexchange

Ejemplares similares