{
  "abstract": "Herein, we report a modular approach to monosubstituted, (hetero)arylated 2-oxabicyclo[2.1.1]hexanes (oxa-BCHs). The strategy combines facile Suzuki–Miyaura cross-couplings to assemble suitable diene precursors that can undergo [2+2] photocycloadditions. Nineteen novel (hetero)aromatic building blocks and fragments are constructed from their respective (hetero)aryl boronates, conveniently accessed from commercial sources. Next, a high-throughput enabled synthetic sequence is performed, demonstrating the gram-scale conversion of 6-quinoline bromide to the corresponding 4-(quinolyl)oxa-BCH adduct. Finally, the physicochemical properties and aqueous stability of the new oxa-BCH biaryl mimetic was compared with those of other medicinally relevant substituents, demonstrating its promise as a robust, three-dimensional, polarity-enhancing motif for medicinal-chemistry applications.",
  "abstract_shown": true,
  "affiliations": [
    "Oncology R&D",
    "Discovery Centre, AstraZeneca",
    "Small Molecule Product Discovery & Development, Astra-Zeneca, Pepparedsleden 1, Mölndal, Sweden",
    "Department of Chemistry, University of Bath, Claverton Down, Bath, UK"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 10,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "David M. Whalley",
      "orcid": "0000-0002-5988-7457"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Olivier Lorthioir",
      "orcid": "0000-0003-4191-4522"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Niall Anderson",
      "orcid": "0000-0001-8403-9698"
    },
    {
      "affs": [
        2
      ],
      "name": "Ioannis Asproudis",
      "orcid": "0009-0001-4708-7516"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Erin Braybrooke"
    },
    {
      "affs": [
        3
      ],
      "name": "Susannah Coote",
      "orcid": "0000-0002-3590-9113"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "James Middleton"
    },
    {
      "affs": [
        2
      ],
      "name": "Okky Dwichandra Putra",
      "orcid": "0000-0002-6968-1858"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Philip J. Rushworth"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Sam Staniland"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/2tebb7gxjh44p.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15010496/v1",
  "fulltext_url": null,
  "id": "2tebb7gxjh44p",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010496/v1",
  "language": null,
  "licence": "CC-BY-NC-ND",
  "licence_label": "CC BY-NC-ND",
  "licence_source": "journal",
  "licence_url": "https://creativecommons.org/licenses/by-nc-nd/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "openalex",
      "1605|Catalytic Cross-Coupling Reactions"
    ]
  ],
  "openalex": "W7222351093",
  "pdf_url": "https://chemrxiv.org/doi/pdf/10.26434/chemrxiv.15010496/v1",
  "pmcid": null,
  "pmid": null,
  "published": "2026-10-15",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/2tebb7gxjh44p.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:24Z",
      "native_id": "10.26434/chemrxiv.15010496",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010496/v1"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Catalytic Cross-Coupling Reactions",
      "subfield": "organic"
    }
  ],
  "title": "A General Suzuki–Miyaura/[2+2] Photocycloaddition Approach to 2-Oxabicyclo[2.1.1]hexane Biaryl Mimetics",
  "title_text": "A General Suzuki–Miyaura/[2+2] Photocycloaddition Approach to 2-Oxabicyclo[2.1.1]hexane Biaryl Mimetics",
  "type": "preprint",
  "updated_at": "2026-10-30T12:17:24Z",
  "url": "https://research.draconitic.com/paper/2tebb7gxjh44p",
  "venue": "ChemRxiv",
  "versions": []
}