Direct electrochemical reductive amination between aldehydes and amines with a H/D-donor solvent
A novel electrochemical synthesis protocol has been achieved for reductive amination between aldehydes and amines in undivided cells at room temperature. Under metal-free and external-reductant-free electrolysis conditions, various important secondary amine products are obtained in moderate-to-high...
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Veröffentlicht in: | Organic & biomolecular chemistry 2020-08, Vol.18 (3), p.5832-5837 |
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Hauptverfasser: | , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | A novel electrochemical synthesis protocol has been achieved for reductive amination between aldehydes and amines in undivided cells at room temperature. Under metal-free and external-reductant-free electrolysis conditions, various important secondary amine products are obtained in moderate-to-high yields. Deuterium-labeling experiments have demonstrated that low-toxicity DMSO acts both as a solvent and a H-donor in the reaction. On this basis, various deuterium-labeled products with good-to-excellent D-incorporation have been synthesized by using DMSO-
d
6
as a solvent. Furthermore, a molecule with GR-antagonistic activity has been synthesized through further sulfonylation.
Electrochemical reductive amination of aldehydes and amines was first realized at room temperature by using DMSO/DMSO-
d
6
as a H/D-donor solvent. |
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ISSN: | 1477-0520 1477-0539 |
DOI: | 10.1039/d0ob01163k |