4.8 Article

Electrosynthesis of Stabilized Diazo Compounds from Hydrazones

Journal

ORGANIC LETTERS
Volume 24, Issue 25, Pages 4665-4669

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01803

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Funding

  1. Natural Sciences and Engineering Research Council of Canada [PGSD3-546986-2020]
  2. Royal Society of Chemistry [M19-0357]
  3. Engineering and Physical Sciences Research Council [EP/S017097/1]
  4. Leverhulme Trust [RPG-2021-146]
  5. University of Greenwich
  6. Natural Sciences and Engineering Research Council of Canada (NSERC) [RGPIN-2017-04272]
  7. FRQNT Centre in Green Chemistry and Catalysis (CGCC) [FRQNT-2020-RS4-265155-CCVC]
  8. Universite Laval

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An electrochemical synthesis method was developed for the efficient conversion of hydrazones into diazo compounds, achieving yields as high as 99%. This method was shown to be both environmentally friendly and practical, as it required mild conditions and demonstrated high electron efficiency (3 F/mol) comparable to commonly used chemical oxidants.
An electrochemical synthesis of diazo compounds from hydrazones in yields as high as 99% was performed. This method was elaborated as a useful synthetic method and demonstrated on various diazo compounds (24 examples). Apart from exhibiting an efficiency that matched that of commonly used harsh and toxic chemical oxidants, this reaction is practically simple to set up, requires mild conditions, and is highly electron efficient (3 F/mol).

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