{
  "abstract": "Herein, we report a second-generation SF5-alkenyl platform reagent granting facile benchtop access to a variety of known and unknown SF5-containing building blocks under mild conditions without any necessity to use pentafluorosulfanylation reagents, such as SF5Cl, on-site. This work overcomes the previous synthetic bottleneck that had prevented a broader use of the triisopropylsilylalkynyl (TASP) reagent. This versatile platform reagent is thermally stable, easy to handle, shows high shelf stability, and can be accessed on a multigram scale. This class of reagents undergoes protodesilylation/nucleophilic substitution reactions with O-, S-, and N-nucleophiles allowing access to (E)-configured α-SF5-enamines (up to >99%), (E)-configured α-SF5-vinyl ethers (up to 90%), another synthetically useful access to (E)-configured β-vinyl sulfides (up to 99%), O,O-acetals (up to 95%), and S,S-acetals (up to 97%) in a single reaction step. Further processing allowed access to S,S-ketene acetals (up to 97%), the corresponding α-SF5-acetic acid esters (up to 88%), as well as α-SF5-acetic acid (92%). Based on these findings, we shed light on the operating reaction mechanism by DFT studies, revealing that the amount of charge accumulated on the α-SF5 carbon controls the efficacy of the reaction with different nucleophiles. In a second part, we reconnected to previous inaccessible alkynyl sulfur pentafluorides by developing a novel in situ elimination strategy and identified the TBDMS derivative as an accessible, stable, and reactive reagent to prepare the complementary (Z)-configured β-vinyl sulfides (up to 85%) in a single reaction step, whereas the pure TMS and TES alkynyl derivatives were found to be inaccessible or unstable under ambient conditions. This report offers a versatile and robust protocol to access important SF5-containing organic motifs employing a commercially available prefunctionalized SF5 reagent.",
  "abstract_shown": true,
  "affiliations": [
    "Karlsruhe Institute of Technology (KIT) , , Kaiserstrasse 12 , ,",
    "Karlsruhe Institute of Technology",
    "University of Zurich",
    "University of Zurich , , Winterthurerstrasse 190 , ,",
    "Karlsruhe Institute of Technology (KIT) , , Engesserstrasse 15 , ,"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 8,
  "authors": [
    {
      "affs": [
        0,
        1,
        2
      ],
      "name": "Philipp Bohn"
    },
    {
      "affs": [
        3,
        2
      ],
      "name": "Richard Kraus"
    },
    {
      "affs": [
        3,
        2
      ],
      "name": "Lujie Xu"
    },
    {
      "affs": [
        3,
        2
      ],
      "name": "Sharon Pinus",
      "orcid": "0000-0001-9771-3098"
    },
    {
      "affs": [
        0,
        2
      ],
      "name": "Max Flügge"
    },
    {
      "affs": [
        3,
        2
      ],
      "name": "André Bütikofer",
      "orcid": "0000-0002-8964-3170"
    },
    {
      "affs": [
        4,
        1
      ],
      "name": "Silke Wolf",
      "orcid": "0000-0003-2890-5031"
    },
    {
      "affs": [
        3,
        2
      ],
      "name": "David Rombach",
      "orcid": "0000-0002-6673-9567"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/6hcj983cj0gtk.bib",
  "cited_by": 5,
  "doi": "10.1021/acsorginorgau.6c00084",
  "fulltext_url": null,
  "id": "6hcj983cj0gtk",
  "issns": [
    "2694-247X"
  ],
  "landing_url": "https://doi.org/10.1021/acsorginorgau.6c00084",
  "language": "en",
  "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|Fluorine in Organic Chemistry"
    ],
    [
      "openalex",
      "3003|Fluorine in Organic Chemistry"
    ]
  ],
  "openalex": "W4413132741",
  "pdf_url": "https://pubs.acs.org/aoiab5/article-pdf/doi/10.1021/acsorginorgau.6c00084/68827454/acsorginorgau.6c00084.pdf",
  "pmcid": null,
  "pmid": null,
  "published": "2026-10-13",
  "publisher": "American Chemical Society",
  "ris": "https://research.draconitic.com/paper/6hcj983cj0gtk.ris",
  "sources": [
    {
      "first_seen": "2026-11-04T13:21:15Z",
      "native_id": "W4413132741",
      "source": "openalex",
      "url": "https://doi.org/10.1021/acsorginorgau.6c00084"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Fluorine in Organic Chemistry",
      "subfield": "organic"
    },
    {
      "field": "medicine",
      "origin": "openalex:3003|Fluorine in Organic Chemistry",
      "subfield": "pharmacology-toxicology"
    }
  ],
  "title": "Silyl Chloroalkenyl and Alkynyl Sulfur Pentafluorides as Versatile Reagents to Access Fundamental SF5 Building Blocks",
  "title_text": "Silyl Chloroalkenyl and Alkynyl Sulfur Pentafluorides as Versatile Reagents to Access Fundamental SF5 Building Blocks",
  "type": "peer-reviewed",
  "updated_at": "2026-11-09T13:21:04Z",
  "url": "https://research.draconitic.com/paper/6hcj983cj0gtk",
  "venue": "ACS Organic & Inorganic Au",
  "versions": []
}