{
  "abstract": "Highly substituted, monocyclic 1,2-azaborines could expand the chemical space available for benzene bioisosterism; however, their synthesis remains an unmet challenge. Here we report a general, modular, transition-metal-free strategy that couples unsaturated imines with dihaloboranes to construct diverse 1,2-azaborines through a borylative benzannulation pathway. This method provides efficient access to tetra-, penta-, and hexa-substituted azaborines, including fused, macrocyclic and heteroatom-substituted scaffolds. High chemoselectivity and convenient handling are achieved by developing well-defined quinoline-buffered borylation reagents. Post-functionalization at the boron and nitrogen positions of 1,2-azaborines, synthesis of a BN-isostere of xibornol, and access to isotopically enriched 10B-1,2-azaborines have been demonstrated.",
  "abstract_shown": true,
  "affiliations": [
    "Chemistry",
    "The University of Chicago",
    "Lilly Research Laboratories,",
    "Eli Lilly and Company"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 10,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "Zhongming Cheng",
      "orcid": "0009-0009-1702-2082"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Masanori Hirao"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Yao Ge"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Liyan Kan"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Kangmin Wen"
    },
    {
      "affs": [
        2,
        3
      ],
      "name": "Qiang Yang"
    },
    {
      "affs": [
        2,
        3
      ],
      "name": "Youming Huang"
    },
    {
      "affs": [
        2,
        3
      ],
      "name": "Jiang Wang"
    },
    {
      "affs": [
        2,
        3
      ],
      "name": "Renato A. Bauer"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Guangbin Dong"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/f3w675n5tk4bp.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15008294/v1",
  "fulltext_url": null,
  "id": "f3w675n5tk4bp",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008294/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",
      "1605|Organoboron and organosilicon chemistry"
    ]
  ],
  "openalex": "W7208712558",
  "pdf_url": "https://chemrxiv.org/doi/pdf/10.26434/chemrxiv.15008294/v1",
  "pmcid": null,
  "pmid": null,
  "published": "2026-09-04",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/f3w675n5tk4bp.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:17Z",
      "native_id": "10.26434/chemrxiv.15008294",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008294/v1"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Organoboron and organosilicon chemistry",
      "subfield": "organic"
    }
  ],
  "title": "A General Approach to Highly Substituted 1,2-Azaborines via Borylative Benzannulation of Unsaturated Imines",
  "title_text": "A General Approach to Highly Substituted 1,2-Azaborines via Borylative Benzannulation of Unsaturated Imines",
  "type": "preprint",
  "updated_at": "2026-10-30T12:17:17Z",
  "url": "https://research.draconitic.com/paper/f3w675n5tk4bp",
  "venue": "ChemRxiv",
  "versions": []
}