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
Hauptverfasser: Hong, Huanliang, Zou, Zirong, Liang, Gen, Pu, Suyun, Hu, Jinhui, Chen, Lu, Zhu, Zhongzhi, Li, Yibiao, Huang, Yubing
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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.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob01163k