{
  "abstract": "Efficient construction of 15N-labeled 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 15N-enriched saturated heterocycles. This transformation is enabled by a methylsulfonyl-based 15N-labeled 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": [
    "University of Chicago , , , ,",
    "Process Research and Development, Merck & Co. , , ,"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 4,
  "authors": [
    {
      "affs": [
        0
      ],
      "name": "Zining Zhang",
      "orcid": "0009-0001-4954-6771"
    },
    {
      "affs": [
        1
      ],
      "name": "Seoung-Tae Kim"
    },
    {
      "affs": [
        1
      ],
      "name": "Jingwei Li",
      "orcid": "0000-0003-2534-5091"
    },
    {
      "affs": [
        0
      ],
      "name": "Guangbin Dong",
      "orcid": "0000-0003-1331-6015"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/91pe9r3xyw9mn.bib",
  "cited_by": 0,
  "doi": "10.1021/jacsau.6c01410",
  "fulltext_url": null,
  "id": "91pe9r3xyw9mn",
  "issns": [
    "2691-3704"
  ],
  "landing_url": "https://pubs.acs.org/jaaucr/article/doi/10.1021/jacsau.6c01410/5463353/Synthesis-of-15N-Labeled-Complex-Saturated-N",
  "language": null,
  "licence": "CC-BY-NC-ND-4.0",
  "licence_label": "CC BY-NC-ND 4.0",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by-nc-nd/4.0/",
  "metadata_licence": null,
  "native_subjects": [],
  "openalex": null,
  "pdf_url": "https://pubs.acs.org/doi/pdf/10.1021/jacsau.6c01410",
  "pmcid": null,
  "pmid": null,
  "published": "2026-11-03",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/91pe9r3xyw9mn.ris",
  "sources": [
    {
      "first_seen": "2026-11-04T00:23:43Z",
      "native_id": "10.1021/jacsau.6c01410",
      "source": "crossref",
      "url": "https://pubs.acs.org/jaaucr/article/doi/10.1021/jacsau.6c01410/5463353/Synthesis-of-15N-Labeled-Complex-Saturated-N"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "issn:2691-3704",
      "subfield": "general"
    }
  ],
  "title": "Synthesis of 15N-Labeled Complex Saturated N -Heterocycles via Late-Stage Carbonyl-to-Nitrogen Swap",
  "title_text": "Synthesis of 15N-Labeled Complex Saturated N -Heterocycles via Late-Stage Carbonyl-to-Nitrogen Swap",
  "type": "peer-reviewed",
  "updated_at": "2026-11-05T00:20:51Z",
  "url": "https://research.draconitic.com/paper/91pe9r3xyw9mn",
  "venue": "JACS Au",
  "versions": []
}