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DOI: 10.1055/s-2006-926378
Erbium(III) Triflate: A Valuable Catalyst for the Synthesis of Aldimines, Ketimines, and Enaminones
Publication History
Publication Date:
08 March 2006 (online)
Abstract
Aldimines, ketimines, and enaminones can be obtained under erbium(III) triflate catalysis. The reaction mechanism is that typical of imine synthesis. The role of the catalyst is demonstrated for the synthesis of aromatic imines. In contrast to CeCl3/NaI addition to unsaturated aldehydes, which results in Michael addition, no Michael adduct was observed under erbium(III) triflate catalysis.
Key words
imines - enaminones - erbium triflate - Lewis acids - catalysis
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References
Some imines were unstable and a one-pot reduction step was necessary for their identification. This was realized by addition of a THF solution of LiBH4 to the mixture, after monitoring the disappearance of the reactants by GC-MS analysis.
13A solution of Er(OTf)3 in water is only weakly acidic (pH 5.9) and the aqueous layers from the work-up were even less acidic (pH 6.7); such values are not compatible with triflic acid being the active catalyst.
14LD50 of erbium salts is 4417 mg/Kg against 4000 mg/Kg for NaCl.
15It is likely that the catalyst can be recovered in higher yields when the reaction is scaled up; we recovered the catalyst in ÷90% yield.