{
  "abstract": "A versatile 1,3-benzdiyne precursor is reported that enables chemoselective, sequential generation of aryne triple bonds on the same aromatic ring under mild conditions. This is achieved from a single aromatic ring bearing an iodonium unit─enabling access to one aryne triple bond via deprotonation─and a \"Kobayashi\"-type ortho-silylaryl triflate unit, from which the second aryne triple bond can be released using fluoride. Each triple bond undergoes regioselective trapping. DFT studies reveal high-to-very high levels of ground state distortion in each aryne system. The approach leverages the unique reactivity of arynes to construct the framework of prized fluoride-activated precursors used in the next step. This strategy grants modular access to otherwise difficult-to-generate 1,2,3,4-substitution motifs.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Chemistry for Life Sciences, Uppsala University, Box 576, 75123Uppsala, Sweden.",
    "Department of Chemistry - Ångström Laboratory, Uppsala University, Box 523, 75120Uppsala, Sweden.",
    "School of Chemistry, University of Bristol, Cantock's Close, Clifton, BristolBS8 1TS, United Kingdom."
  ],
  "article_type": "research article",
  "arxiv": null,
  "author_total": 6,
  "authors": [
    {
      "affs": [
        0
      ],
      "name": "Fredrik Barnå",
      "orcid": "0009-0006-5069-2190"
    },
    {
      "affs": [
        0
      ],
      "name": "Manoj D Patil",
      "orcid": "0000-0003-1669-6076"
    },
    {
      "affs": [
        0
      ],
      "name": "Fredric J L Ingner"
    },
    {
      "affs": [
        1
      ],
      "name": "Andreas Orthaber",
      "orcid": "0000-0001-5403-9902"
    },
    {
      "affs": [
        2
      ],
      "name": "Paul J Gates",
      "orcid": "0000-0001-8619-7745"
    },
    {
      "affs": [
        0
      ],
      "name": "Lukasz T Pilarski",
      "orcid": "0000-0002-9353-2238"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/c4th8ra853e7r.bib",
  "cited_by": 0,
  "doi": "10.1021/acs.joc.6c00616",
  "fulltext_url": "https://europepmc.org/articles/PMC13595903",
  "id": "c4th8ra853e7r",
  "issns": [
    "0022-3263",
    "1520-6904"
  ],
  "landing_url": "https://europepmc.org/article/MED/42917090",
  "language": "eng",
  "licence": "CC-BY",
  "licence_label": "CC BY",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "openalex",
      "1605|Cyclization and Aryne Chemistry"
    ]
  ],
  "openalex": "W7211869568",
  "pdf_url": "https://europepmc.org/articles/PMC13595903?pdf=render",
  "pmcid": "PMC13595903",
  "pmid": "42917090",
  "published": "2026-09-01",
  "publisher": null,
  "ris": "https://research.draconitic.com/paper/c4th8ra853e7r.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:21:02Z",
      "native_id": "MED:42917090",
      "source": "europepmc",
      "url": "https://europepmc.org/article/MED/42917090"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Cyclization and Aryne Chemistry",
      "subfield": "organic"
    }
  ],
  "title": "Chemoselective Generation of the 1,3-Benzdiyne Synthon.",
  "title_text": "Chemoselective Generation of the 1,3-Benzdiyne Synthon.",
  "type": "peer-reviewed",
  "updated_at": "2026-10-30T12:21:02Z",
  "url": "https://research.draconitic.com/paper/c4th8ra853e7r",
  "venue": "The Journal of organic chemistry",
  "versions": []
}