{
  "abstract": "‡Process Research and Development, Merck & Co., Rahway, New Jersey 07065, United States ABSTRACT: Efficient construction of 15N-labelled complex saturated N-heterocycles remains a substantial challenge. Here we report a late-stage carbonyl-to-15N skeletal modification strategy that converts complex cyclic ketones directly into 15Nenriched saturated heterocycles. This transformation is enabled by a methylsulfonyl-based 15N-labelled azonation reagent that suppresses unwanted overoxidation without compromising the desired C-C bond cleavage pathway. The reaction exhibits a broad substrate scope and tolerates a wide range of functional groups, serving as an effective tool for late-stage skeletal modifications of complex natural products and drug-like molecules. Mechanistic insights on the sequential double C–C activation events have been elucidated by preliminary computational studies.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Chemistry",
    "University of Chicago"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 4,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "Zining Zhang",
      "orcid": "0009-0001-4954-6771"
    },
    {
      "name": "Seoung-Tae Kim"
    },
    {
      "name": "Jingwei Li"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Guangbin Dong"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/fy8ntantkz9qg.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15008499/v1",
  "fulltext_url": null,
  "id": "fy8ntantkz9qg",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008499/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",
      "3003|Chemical Reactions and Isotopes"
    ]
  ],
  "openalex": "W7211933262",
  "pdf_url": "https://chemrxiv.org/doi/pdf/10.26434/chemrxiv.15008499/v1",
  "pmcid": null,
  "pmid": null,
  "published": "2026-09-08",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/fy8ntantkz9qg.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:17Z",
      "native_id": "10.26434/chemrxiv.15008499",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008499/v1"
    }
  ],
  "subjects": [
    {
      "field": "medicine",
      "origin": "openalex:3003|Chemical Reactions and Isotopes",
      "subfield": "pharmacology-toxicology"
    }
  ],
  "title": "Synthesis of 15N-Labelled Complex Saturated N-Heterocycles via Late-Stage Carbonyl-to-Nitrogen Swap",
  "title_text": "Synthesis of 15N-Labelled Complex Saturated N-Heterocycles via Late-Stage Carbonyl-to-Nitrogen Swap",
  "type": "preprint",
  "updated_at": "2026-10-30T12:17:17Z",
  "url": "https://research.draconitic.com/paper/fy8ntantkz9qg",
  "venue": "ChemRxiv",
  "versions": []
}