{
  "abstract": "The activation of diaryl diselenides with N-bromosuccinimide generates two competing electrophiles, and with α-allenols as the π-nucleophiles, product mixtures of brominated and selenylated dihydrofurans can arise. This selectivity challenge was quickly resolved through a Bayesian optimization campaign over seven reaction parameters covering >2000 discrete combinations. Fifteen randomly sampled experiments were sufficient for Gaussian-process surrogate models that, when asked to simultaneously maximize yield and selectivity, recommended conditions that delivered the 3-selanyl-2,5-dihydrofuran in up to 74% yield with complete suppression of the vinyl bromide. The identified protocol for the 5-endo-trig cyclization transferred without re-optimization to a range of structurally diverse α-allenols (50–81% isolated yield) and proved to be applicable to other dichalcogenides, as well as to the 6-endo-trig cyclization of related allene homologues.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Chemistry, University of Helsinki, A. I. Virtasen aukio 1, Helsinki, Finland, 00560",
    "IMC Krems University of Applied Sciences",
    "Department of Materials Science & Environmental Engineering",
    "Tampere University"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 5,
  "authors": [
    {
      "affs": [
        0
      ],
      "name": "Benedikt Gocht"
    },
    {
      "affs": [
        0
      ],
      "name": "Andrei Costea"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Anna Tyshchenko"
    },
    {
      "affs": [
        2,
        3
      ],
      "name": "Janne M. Naapuri",
      "orcid": "0009-0008-3419-7311"
    },
    {
      "affs": [
        0
      ],
      "name": "Jan Deska",
      "orcid": "0000-0003-4622-2365"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/b2k1yg8y1n3aq.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15011183/v1",
  "fulltext_url": null,
  "id": "b2k1yg8y1n3aq",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15011183/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",
      "3005|Organoselenium and organotellurium chemistry"
    ]
  ],
  "openalex": "W7224090810",
  "pdf_url": null,
  "pmcid": null,
  "pmid": null,
  "published": "2026-10-28",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/b2k1yg8y1n3aq.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:26Z",
      "native_id": "10.26434/chemrxiv.15011183",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15011183/v1"
    }
  ],
  "subjects": [
    {
      "field": "medicine",
      "origin": "openalex:3005|Organoselenium and organotellurium chemistry",
      "subfield": "pharmacology-toxicology"
    }
  ],
  "title": "Learning Chemoselectivity in a Low-Data Regime: Bayesian Optimization of the NBS-Activated Selenocyclization of α-Allenols",
  "title_text": "Learning Chemoselectivity in a Low-Data Regime: Bayesian Optimization of the NBS-Activated Selenocyclization of α-Allenols",
  "type": "preprint",
  "updated_at": "2026-10-30T12:17:26Z",
  "url": "https://research.draconitic.com/paper/b2k1yg8y1n3aq",
  "venue": "ChemRxiv",
  "versions": []
}