{
  "abstract": "Herein, we report the first catalytic heterodifunctionalization and homodifunctionalization of readily available 1-substituted enyne-type propargylic derivatives, proceeding via a multicomponent remote C2,C5-addition/substitution pathway. This palladium-catalyzed protocol enables the modular and straightforward assembly of tri-, tetra-, and penta-substituted 1,3-dienes with diverse functional groups from two heteroatom nucleophiles or one heteroatom nucleophile and one carbon nucleophile. The reaction exhibits high chemo-, regio-, and stereoselectivity, accommodates a broad spectrum of O-, N-, S-, and C-nucleophiles, and delivers highly substituted (Z, E)-1,3-dienes with precise stereocontrol. Notably, switching from O- to S-nucleophiles triggers a nucleophile-directed stereodivergence. The synthetic utility is further demonstrated through diverse downstream transformations, efficient synthesis of bioactive molecules, and late-stage functionalization of natural products. Mechanistic studies reveal the involvement of heteroatom-containing pentacoordinate π-allyl palladium and π-alkynyl palladium intermediates in this heterodifunctionalization process.",
  "abstract_shown": true,
  "affiliations": [
    "Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, and State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan",
    "Yunnan University",
    "School of Artificial Intelligence",
    "Shenzhen University",
    "Southwest United Graduate School"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 13,
  "authors": [
    {
      "affs": [
        0,
        1,
        2,
        3
      ],
      "name": "Shan Wang"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Ming Jiang"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Yifei Zheng"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Gengchen Li"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Yubin Lin"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Long Li"
    },
    {
      "affs": [
        2,
        3
      ],
      "name": "Haoming Cheng"
    },
    {
      "affs": [
        2,
        3
      ],
      "name": "Xiaoguang Li"
    },
    {
      "affs": [
        2,
        3
      ],
      "name": "Zheng Wang"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Yingcheng Wang"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Fangzhi Peng"
    },
    {
      "affs": [
        0,
        1,
        4
      ],
      "name": "Zhihui Shao"
    },
    {
      "name": "long li",
      "orcid": "0009-0003-8193-7814"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/364787c9ghbtv.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15010221/v1",
  "fulltext_url": null,
  "id": "364787c9ghbtv",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010221/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",
      "1605|Catalytic Cross-Coupling Reactions"
    ]
  ],
  "openalex": "W7221576618",
  "pdf_url": "https://chemrxiv.org/doi/pdf/10.26434/chemrxiv.15010221/v1",
  "pmcid": null,
  "pmid": null,
  "published": "2026-10-11",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/364787c9ghbtv.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:22Z",
      "native_id": "10.26434/chemrxiv.15010221",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010221/v1"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Catalytic Cross-Coupling Reactions",
      "subfield": "organic"
    }
  ],
  "title": "Diverse Remote Difunctionalization of Enyne-type Propargylic Carbonates: Regio-, Chemo-, and Stereoselective Access to Highly Functionalized Multisubstituted 1,3-Dienes",
  "title_text": "Diverse Remote Difunctionalization of Enyne-type Propargylic Carbonates: Regio-, Chemo-, and Stereoselective Access to Highly Functionalized Multisubstituted 1,3-Dienes",
  "type": "preprint",
  "updated_at": "2026-10-30T12:17:22Z",
  "url": "https://research.draconitic.com/paper/364787c9ghbtv",
  "venue": "ChemRxiv",
  "versions": []
}