{
  "abstract": "A general fluorodeboronation protocol that converts readily available alkenyl boronates into fluorinated alkenes under mild aqueous biphasic conditions is proposed. The method employs 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis-tetrafluoroborate (F-TEDA) as a fluorine source in the presence of KHF 2 , providing broad access to functionalized alkenyl fluorides from β-substituted and β,β-disubstituted alkenyl boronates, including cyclic, heterocyclic, aryl-, heteroaryl-, and alkyl-substituted derivatives, with good functional-group tolerance and preparative scalability. In contrast, αsubstituted alkenyl boronates displayed divergent reactivity, furnishing allylic fluorides through a rearrangement pathway. Mechanistic experiments and DFT calculations support initial electrophilic fluorination of the C=C bond followed by either BF 3 elimination or 1,2-hydride shift, depending on the substitution pattern and stability of the resulting cationic intermediate.",
  "abstract_shown": true,
  "affiliations": [
    "Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyїv, Ukraine, 01601",
    "Enamine Scientific Research Institute, Winston Churchill Street 67, Kyїv, Ukraine, 02094",
    "Enamine Ltd., Winston Churchill Street 78, Kyїv, Ukraine, 02094",
    "Institute of Organic Chemistry, NAS of Ukraine, Akademik Kukhar Street 5, Kyїv, Ukraine, 02066",
    "Department of Chemistry",
    "Mellon College of Science, Carnegie Mellon University"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 9,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "Oleksandr S. Liashuk"
    },
    {
      "affs": [
        2,
        3
      ],
      "name": "Oleksandr P. Demchuk"
    },
    {
      "affs": [
        0,
        2
      ],
      "name": "Varvara Trachova"
    },
    {
      "affs": [
        0,
        2
      ],
      "name": "Illya Zahorniy"
    },
    {
      "affs": [
        0,
        2
      ],
      "name": "Oleksandr Hryshchuk"
    },
    {
      "affs": [
        4,
        5
      ],
      "name": "Tetiana Zubatiuk"
    },
    {
      "affs": [
        0,
        2
      ],
      "name": "Andrii Kozytskyi"
    },
    {
      "affs": [
        4,
        5
      ],
      "name": "Oleksandr Isayev"
    },
    {
      "affs": [
        0,
        1,
        2
      ],
      "name": "Oleksandr O. Grygorenko",
      "orcid": "0000-0002-6036-5859"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/88605h6db9466.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15010429/v1",
  "fulltext_url": null,
  "id": "88605h6db9466",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010429/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",
      "3003|Fluorine in Organic Chemistry"
    ]
  ],
  "openalex": "W7221783696",
  "pdf_url": "https://chemrxiv.org/doi/pdf/10.26434/chemrxiv.15010429/v1",
  "pmcid": null,
  "pmid": null,
  "published": "2026-10-13",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/88605h6db9466.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:24Z",
      "native_id": "10.26434/chemrxiv.15010429",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010429/v1"
    }
  ],
  "subjects": [
    {
      "field": "medicine",
      "origin": "openalex:3003|Fluorine in Organic Chemistry",
      "subfield": "pharmacology-toxicology"
    }
  ],
  "title": "Substrate-Controlled Electrophilic Fluorination of Alkenyl Boronates: Direct versus 1,2- H -Migrative Fluorodeboronation",
  "title_text": "Substrate-Controlled Electrophilic Fluorination of Alkenyl Boronates: Direct versus 1,2- H -Migrative Fluorodeboronation",
  "type": "preprint",
  "updated_at": "2026-10-30T12:17:24Z",
  "url": "https://research.draconitic.com/paper/88605h6db9466",
  "venue": "ChemRxiv",
  "versions": []
}