4.6 Article

Direct electrochemical reductive amination between aldehydes and amines with a H/D-donor solvent

期刊

ORGANIC & BIOMOLECULAR CHEMISTRY
卷 18, 期 30, 页码 5832-5837

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob01163k

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资金

  1. Foundation of the Department of Education of Guangdong Province [2017KZDXM085, 2018KZDXM070, 2019KZDXM052]
  2. Foundation of Guangdong Basic and Applied Basic Research [2019A1515110516, 2019A1515110266, 2019A1515110522]
  3. Foundation for Young Talents [2019KQNCX159, 2019KQNCX160, 2018KQNCX273]
  4. Science Foundation for Young Teachers of Wuyi University [pdjh2020a0595]
  5. National College Students Innovation and Entrepreneurship Training Program [201911349031, 3344100114]

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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.

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