{
  "abstract": "High Resolution Image Download MS PowerPoint Slide Regioselective access to electron-deficient and highly substituted pyrroles from simple building blocks remains challenging. Here we show that O -vinylhydroxylamines enable the de novo construction of pyrroles through an aza-Michael/oxaza-Cope [3,3]-sigmatropic rearrangement/aromatization cascade with activated alkynes. This one-pot transformation proceeds rapidly at room temperature using catalytic amounts of a mild organic base and furnishes dihydropyrrole hemiaminal intermediates that can be directly converted to pyrroles or selectively functionalized. The method accommodates a broad range of O -vinylhydroxylamines and activated alkyne partners and enables access to substitution patterns that previously required harsh conditions or hazardous acetylene-based methods. These results establish O -vinylhydroxylamines as versatile building blocks for the synthesis of highly functionalized pyrroles.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Chemistry",
    "Rice University",
    "Enamine Ltd, Winston Churchill St. 78, 02094 Kyiv, Ukraine",
    "Institute of Functional Materials Chemistry, State Scientific Institution State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Nauky Ave., 60, 61072 Kharkiv, Ukraine",
    "Taras Shevchenko National University of Kyiv, Faculty of Chemistry, Volodymyrska, 60, 01601 Kyiv, Ukraine"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 5,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "Charlotte Randolph"
    },
    {
      "affs": [
        2,
        3
      ],
      "name": "Oleksandr V. Buravov",
      "orcid": "0009-0008-8433-5524"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Zachary Grimm",
      "orcid": "0009-0005-1751-2058"
    },
    {
      "affs": [
        2,
        4
      ],
      "name": "Pavel K. Mykhailiuk",
      "orcid": "0000-0003-1821-9011"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "László Kürti",
      "orcid": "0000-0002-3412-5894"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/ccxpr8smn7c9n.bib",
  "cited_by": 7,
  "doi": "10.1021/jacs.6c06697",
  "fulltext_url": null,
  "id": "ccxpr8smn7c9n",
  "issns": [
    "0002-7863",
    "1520-5126",
    "1943-2984"
  ],
  "landing_url": "https://doi.org/10.1021/jacs.6c06697",
  "language": "en",
  "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|Synthesis and Characterization of Pyrroles"
    ]
  ],
  "openalex": "W7162196859",
  "pdf_url": "https://pubs.acs.org/doi/pdf/10.1021/jacs.6c06697?ref=article_openPDF",
  "pmcid": "PMC13244452",
  "pmid": "42175936",
  "published": "2026-05-23",
  "publisher": "American Chemical Society",
  "ris": "https://research.draconitic.com/paper/ccxpr8smn7c9n.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T13:26:44Z",
      "native_id": "W7162196859",
      "source": "openalex",
      "url": "https://doi.org/10.1021/jacs.6c06697"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Synthesis and Characterization of Pyrroles",
      "subfield": "organic"
    }
  ],
  "title": "O -Vinylhydroxylamines for De Novo Pyrrole Synthesis",
  "title_text": "O -Vinylhydroxylamines for De Novo Pyrrole Synthesis",
  "type": "peer-reviewed",
  "updated_at": "2026-11-08T13:20:39Z",
  "url": "https://research.draconitic.com/paper/ccxpr8smn7c9n",
  "venue": "Journal of the American Chemical Society",
  "versions": []
}