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Regioselective Functionalization of Propargyl Amines via Electrochemically Generated Alkynyl Iminium Cations
Tomohiro Takahashi1, Chisato Yokota1, Kazuhiro Okamoto1
1Department of Science, University of Toyama, 3190 Gofuku, Toyama, 930-0887, Japan.
Abstract:
Electrochemical oxidation of propargyl amines affords alkynyl iminium cation species, which undergo regioselective nucleophilic addition to yield the corresponding N-α substituted propargyl amines. Additionally, an unprecedented enaminal formation was observed in the presence of water, providing functionalized aldehydes in a single step. Cyclic voltammetry (CV) analysis indicates that dimethyl sulfoxide (DMSO) plays a crucial role in enhancing reaction efficiency by stabilizing the otherwise unstable alkynyl iminium cations.
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