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Dynamic Covalent Chemistry of Aldehyde Enamines: Bi III ‐ and Sc III ‐Catalysis of Amine–Enamine Exchange
Author(s) -
Zhang Yang,
Xie Sheng,
Yan Mingdi,
Ramström Olof
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201702363
Subject(s) - enamine , chemistry , imine , covalent bond , aldehyde , amine gas treating , dynamic covalent chemistry , catalysis , organic chemistry , polymer chemistry , computational chemistry , molecule , supramolecular chemistry
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 m m ) 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.