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March 15, 2026ACS electrochemistry.0 citations

eCyanation: A Dual Strategy for Electrochemical Cyanation of Amines Using Potassium Thiocyanate

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SHShusuke HattoriMGMarco GalzignatoKLKevin Lam

Key Points

  • To present an innovative electrochemical approach for the cyanation of amines using potassium thiocyanate.
  • Developed eCyanation process utilizing potassium thiocyanate for safer cyanation
  • Generated cyanogenic species under mild anodic conditions
  • Introduced a two-step bromine-mediated activation for oxidation-sensitive substrates.
  • Successfully demonstrated N- and S-cyanation without handling toxic cyanide salts
  • Provided a practical alternative to highly toxic cyanogen halides
  • Offered a complementary method for substrates sensitive to oxidation.

Abstract

Electrophilic cyanation has long relied on highly toxic cyanogen halides, which limits practical use. Here we present eCyanation, an electrochemical approach that uses inexpensive, bench-stable potassium thiocyanate as the cyanide source. Under mild anodic conditions, electrophilic cyanating species are generated from thiocyanate, enabling N- and S-cyanation without handling cyanide salts or isolating cyanogen halides. For oxidation-sensitive substrates, we also provide a complementary two-step variant: bromine-mediated activation of thiocyanate generates a reactive cyanating solution, which is then combined with the nucleophile after electrolysis. Together, these two operational modes offer a practical entry point to electrophilic cyanation chemistry from thiocyanate.

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Cite This Study

Hattori et al. (2026) studied this question.

synapsesocial.com/papers/69b5ff8083145bc643d1c118https://doi.org/10.1021/acselectrochem.6c00017
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