{
  "abstract": "Broadly applicable and selective C–N bond formation remains a cornerstone challenge in organic synthesis. Although electrochemical methods have recently emerged as an efficient way for achieving decarboxylative C–N coupling, transforming allenoic acids into N-functionalized products remains elusive. Herein, we report the development of an electrochemical strategy for the decarboxylative N-propargylation of N-heterocycles using readily available 2,3-allenoic acids. By correlating the oxidation potentials of allenoic acids and nucleophilic coupling partners, we derived predictive criteria for anticipating reaction efficiency across a broad substrate scope. Mechanistic studies (cyclic voltammetry, in situ infrared (IR) kinetics, and density functional theory (DFT) calculations) support a two-step sequence involving oxidative decarboxylation to an allenyl radical rapidly oxidized to a highly electrophilic allenyl/propargyl cation and regioselective heterocycle attack yielding N-propargylated products. This work showcases a straightforward method for accessing reactive allenyl cation intermediates and expands the toolkit for sustainable electrosynthetic C–N bond formation.",
  "abstract_shown": true,
  "affiliations": [],
  "article_type": null,
  "arxiv": null,
  "author_total": 4,
  "authors": [
    {
      "name": "Sarah Abdoun"
    },
    {
      "name": "Christophe Bour"
    },
    {
      "name": "Robert Mayer"
    },
    {
      "name": "Marie Vayer"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/715kh1yj6h1bb.bib",
  "cited_by": 0,
  "doi": "10.1021/acsorginorgau.5c00117",
  "fulltext_url": null,
  "id": "715kh1yj6h1bb",
  "issns": [
    "2694-247X"
  ],
  "landing_url": "https://hal.science/hal-05771765v1",
  "language": "en",
  "licence": "CC-BY-NC-ND-4.0",
  "licence_label": "CC BY-NC-ND 4.0",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by-nc-nd/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "hal",
      "0.chim"
    ],
    [
      "hal",
      "1.chim.orga"
    ],
    [
      "hal",
      "1.chim.othe"
    ],
    [
      "openalex",
      "1605|Radical Photochemical Reactions"
    ]
  ],
  "openalex": "W7139028805",
  "pdf_url": "https://hal.science/hal-05771765/document",
  "pmcid": null,
  "pmid": null,
  "published": "2026-10-06",
  "publisher": "ACS Publications",
  "ris": "https://research.draconitic.com/paper/715kh1yj6h1bb.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:49Z",
      "native_id": "hal-05771765",
      "source": "hal",
      "url": "https://hal.science/hal-05771765v1"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "hal:1.chim.orga",
      "subfield": "organic"
    }
  ],
  "title": "Electrochemical N-Propargylation of N-Heterocycles via Decarboxylation of Allenoic Acids",
  "title_text": "Electrochemical N-Propargylation of N-Heterocycles via Decarboxylation of Allenoic Acids",
  "type": "peer-reviewed",
  "updated_at": "2026-10-30T12:17:49Z",
  "url": "https://research.draconitic.com/paper/715kh1yj6h1bb",
  "venue": "ACS Organic & Inorganic Au",
  "versions": []
}