{
  "abstract": "We report the design and scalable synthesis of novel sulfilimine-based hypervalent iodine reagents (INSert, based on the I-N=S motif), that are bench-stable, non-explosive and can act as bifunctional electrophilic nitrogen donors. Their distinctive architecture combines a benziodoxolone moiety to induce electrophilicity at the nitrogen atom, with a sulfilimine group as a versatile, latent synthetic handle for downstream diversification. We first demonstrate the utility of this reagent class through the formal anti-Markovnikov hydrosulfilimination of alkenes via alkyldimethylborane intermediates, followed by subsequent transformation of the resulting N-alkylsulfilimine into various nitrogen-containing scaffolds. We also report preliminary N-insertion reactions with an indole and an imidazole. These results clearly show that the reagents’ modular iodinane-sulfilimine architecture can open new avenues for the incorporation of nitrogen into organic molecules through multiple distinct reaction manifolds.",
  "abstract_shown": true,
  "affiliations": [],
  "article_type": null,
  "arxiv": null,
  "author_total": 8,
  "authors": [
    {
      "name": "Andrii Suponytskyi"
    },
    {
      "name": "Patrick W. Fritz"
    },
    {
      "name": "Mykola Avramenko"
    },
    {
      "name": "Lucia Invernizzi"
    },
    {
      "name": "Gian Carmine Conigliaro"
    },
    {
      "name": "Lara Kirchberg"
    },
    {
      "name": "Leonard Kreft"
    },
    {
      "name": "Bill Morandi",
      "orcid": "0000-0003-3968-1424"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/a4dtd95z9ktxf.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15009957/v1",
  "fulltext_url": null,
  "id": "a4dtd95z9ktxf",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009957/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|Synthesis and Catalytic Reactions"
    ]
  ],
  "openalex": "W7220745888",
  "pdf_url": "https://chemrxiv.org/doi/pdf/10.26434/chemrxiv.15009957/v1",
  "pmcid": null,
  "pmid": null,
  "published": "2026-10-05",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/a4dtd95z9ktxf.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:22Z",
      "native_id": "10.26434/chemrxiv.15009957",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009957/v1"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Synthesis and Catalytic Reactions",
      "subfield": "organic"
    }
  ],
  "title": "Sulfilimine benziodoxolones: stable electrophilic bifunctional reagents for nitrogen incorporation",
  "title_text": "Sulfilimine benziodoxolones: stable electrophilic bifunctional reagents for nitrogen incorporation",
  "type": "preprint",
  "updated_at": "2026-10-30T12:17:22Z",
  "url": "https://research.draconitic.com/paper/a4dtd95z9ktxf",
  "venue": "ChemRxiv",
  "versions": []
}