4.7 Article

Electrodimerization of N-Alkoxyamides for the Synthesis of Hydrazines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 22, Pages 16068-16076

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01294

Keywords

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Funding

  1. National Natural Science Foundation of China [21971227]
  2. Anhui Provincial Natural Science Foundation [1808085MB30]
  3. China Postdoctoral Science Foundation [2020M682004]
  4. Fundamental Research Funds for the Central Universities [WK2340000090]

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An efficient and valuable N-N dimerization reaction of N-alkoxyamides is reported under undivided electrolytic conditions. A crucial role is played by an N-centered radical generated from the cleavage of the N-H bond under electrolytic conditions. Various N-alkoxyamides bearing different substituents are suitable in this transformation, furnishing the corresponding hydrazines in up to 92% yield.
An efficient and valuable N-N dimerization reaction of N-alkoxyamides is reported under undivided electrolytic conditions. This electrochemical strategy provides a powerful way to access a wide range of advanced, highly functionalized hydrazines. Remarkably, an N-centered radical generated from the cleavage of the N-H bond under electrolytic conditions plays a crucial role in this transformation. Furthermore, various N-alkoxyamides bearing different substituents are suitable in this transformation, furnishing the corresponding hydrazines in up to 92% yield.

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