{
  "abstract": "We report the discovery of a fundamentally unique nucleophilic aromatic substitution (S N Ar) reaction. It was found that a-arylmalononitriles and haloheterocycles undergo a mild, additive- and base-free C–C bond forming reaction via in situ co-activation (ISCA) to a carbanion and a pyridinium, which rapidly react through a neutral and low-barrier Meisenheimer complex to ultimately yield the S N Ar product. This study includes a background analysis of ISCA-S N Ar and a-aryl-a-heteroarylmalononitriles, discovery and optimization of efficient coupling conditions, a study of various physical organic parameters governing the transformation, scope of the reaction, and select malononitrile functional group interconversions. These detailed studies lay the groundwork for developing this, and related reactions, for use in high-value organic synthesis.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Chemistry",
    "University of Minnesota"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 3,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "Avneesh Kumar"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Akash Gogate"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Alexander Grenning",
      "orcid": "0000-0002-8182-9464"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/5yhvqfnfrkd2s.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15000950/v2",
  "fulltext_url": null,
  "id": "5yhvqfnfrkd2s",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15000950/v2",
  "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|Catalytic Cross-Coupling Reactions"
    ]
  ],
  "openalex": "W7213313140",
  "pdf_url": "https://chemrxiv.org/doi/pdf/10.26434/chemrxiv.15000950/v2",
  "pmcid": null,
  "pmid": null,
  "published": "2026-09-15",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/5yhvqfnfrkd2s.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:19Z",
      "native_id": "10.26434/chemrxiv.15000950",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15000950/v2"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Catalytic Cross-Coupling Reactions",
      "subfield": "organic"
    }
  ],
  "title": "In Situ Co-Activation–Nucleophilic Aromatic Substitution (ISCA–SNAR): Synthesis of a-Aryl-a-Heteroarylmalononitriles.",
  "title_text": "In Situ Co-Activation–Nucleophilic Aromatic Substitution (ISCA–SNAR): Synthesis of a-Aryl-a-Heteroarylmalononitriles.",
  "type": "preprint",
  "updated_at": "2026-10-30T12:17:19Z",
  "url": "https://research.draconitic.com/paper/5yhvqfnfrkd2s",
  "venue": "ChemRxiv",
  "versions": []
}