{
  "abstract": "Organic nitriles are an important class of compounds found in pharmaceuticals and agrochemicals, as well as useful intermediates in synthesis. Decarboxylative cyanation as a method to generate nitriles enables the use of widely available carboxylic acids as starting materials. Although this method has been well-explored synthetically, current methodologies often feature poor atom economy or require harsh reaction conditions. Herein, an electrochemical method for the decarboxylative cyanation of Cbz-protected alanine that uses inexpensive KCN as the cyanide source has been developed. The operationally simple procedure only requires electrolyzing a mixture of the amino acid with the cyanide in DMSO/EtOH as the solvent, without any additional chemicals such as base or supporting electrolyte, resulting in excellent green chemistry metrics. Using inexpensive graphite and stainless-steel as electrodes, excellent conversion and selectivity towards the desired nitrile product were obtained. Translation of the process to a flow electrolysis cell confirmed that the electrochemical protocol is scalable. Thus, gram amounts of material were obtained in a parallel plate reactor, with a space-time yield of 1026 g L-1 h-1. The space-time yield in the flow system was ca. 70 times larger than its batch counterpart, confirming the suitability of flow electrolysis cells for scale-up purposes.",
  "abstract_shown": true,
  "affiliations": [
    "School of Chemistry and Molecular Biosciences",
    "University of Queensland"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 3,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "Peter D. Giang"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Cristóbal Hormazábal-Campos"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "David Cantillo",
      "orcid": "0000-0001-7604-8711"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/0ck2bwgazjwjc.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15011156/v1",
  "fulltext_url": null,
  "id": "0ck2bwgazjwjc",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15011156/v1",
  "language": null,
  "licence": "CC-BY",
  "licence_label": "CC BY",
  "licence_source": "journal",
  "licence_url": "https://creativecommons.org/licenses/by/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "openalex",
      "1605|Radical Photochemical Reactions"
    ]
  ],
  "openalex": "W7224088241",
  "pdf_url": "https://chemrxiv.org/doi/pdf/10.26434/chemrxiv.15011156/v1",
  "pmcid": null,
  "pmid": null,
  "published": "2026-10-27",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/0ck2bwgazjwjc.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:26Z",
      "native_id": "10.26434/chemrxiv.15011156",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15011156/v1"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Radical Photochemical Reactions",
      "subfield": "organic"
    }
  ],
  "title": "Sustainable and Scalable Electrochemical Decarboxylative Cyanation of an Amino Acid Using KCN as Both Cyanide Source and Base",
  "title_text": "Sustainable and Scalable Electrochemical Decarboxylative Cyanation of an Amino Acid Using KCN as Both Cyanide Source and Base",
  "type": "preprint",
  "updated_at": "2026-10-30T12:17:26Z",
  "url": "https://research.draconitic.com/paper/0ck2bwgazjwjc",
  "venue": "ChemRxiv",
  "versions": []
}