{
  "abstract": "Fluorination of the terminal acceptor unit is a reliable way to deepen the LUMO level and enhance the electron mobility of quinoidal n-type organic semiconductors, yet no fluorinated analogue of the thieno[3,2- b ]thiophene-fused acceptor TTC has been reported. Two routes to such an acceptor were examined. In a late-stage approach, the tricyclic 1,3-dione core was assembled first; under Pd(0)-catalyzed stannylation conditions, however, its doubly activated methylene group rather than the C–Br bond was engaged, as confirmed by a control experiment with a monoketone analogue. In an early-stage approach, a bicyclic thienothiophene stannane was subjected to silver-mediated fluorodestannylation with Selectfluor TM . Instead of the expected aryl fluoride, an α-fluorothiophenone was isolated and its structure established by HRMS and multinuclear NMR spectroscopy. Its formation is consistent with the interception of the aryl–silver intermediate by oxygen, followed by tautomerization and α-fluorination. In the absence of silver, the stannane underwent oxidative homocoupling without fluorine incorporation. These results reveal a limitation of silver-mediated fluorodestannylation on π-excessive fused thiophenes.",
  "abstract_shown": true,
  "affiliations": [],
  "article_type": null,
  "arxiv": null,
  "author_total": 7,
  "authors": [
    {
      "name": "Hai-Tung Chuan"
    },
    {
      "name": "Li-Shin Shen"
    },
    {
      "name": "Huai-En Yu"
    },
    {
      "name": "Chia-Chi Chen"
    },
    {
      "name": "Jin-Pei Deng"
    },
    {
      "name": "Rong-Jiun Sheu",
      "orcid": "0000-0002-3859-4399"
    },
    {
      "name": "Chung-Shan Yu",
      "orcid": "0000-0002-2964-485X"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/bhesg1g2pxgvk.bib",
  "cited_by": 0,
  "doi": "10.3762/bjoc.22.124",
  "fulltext_url": null,
  "id": "bhesg1g2pxgvk",
  "issns": [
    "1860-5397"
  ],
  "landing_url": "https://www.beilstein-journals.org/bjoc/articles/22/124",
  "language": null,
  "licence": "CC-BY-4.0",
  "licence_label": "CC BY 4.0",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by/4.0",
  "metadata_licence": null,
  "native_subjects": [],
  "openalex": null,
  "pdf_url": "https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-22-124.pdf",
  "pmcid": null,
  "pmid": null,
  "published": "2026-11-02",
  "publisher": "Beilstein Institut",
  "ris": "https://research.draconitic.com/paper/bhesg1g2pxgvk.ris",
  "sources": [
    {
      "first_seen": "2026-11-02T12:22:37Z",
      "native_id": "10.3762/bjoc.22.124",
      "source": "crossref",
      "url": "https://www.beilstein-journals.org/bjoc/articles/22/124"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "issn:1860-5397",
      "subfield": "organic"
    }
  ],
  "title": "Silver-mediated fluorodestannylation of an electron-rich thieno[3,2- b ]thiophene diverts to oxygenation: an α-fluorothiophenone instead of an aryl fluoride",
  "title_text": "Silver-mediated fluorodestannylation of an electron-rich thieno[3,2- b ]thiophene diverts to oxygenation: an α-fluorothiophenone instead of an aryl fluoride",
  "type": "peer-reviewed",
  "updated_at": "2026-11-04T00:23:57Z",
  "url": "https://research.draconitic.com/paper/bhesg1g2pxgvk",
  "venue": "Beilstein Journal of Organic Chemistry",
  "versions": []
}