Alkenylation of C(sp 3 )-H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts.

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  • Author(s): Liu C;Liu C;Liu C; Wang Q; Wang Q
  • Source:
    Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2018 Apr 16; Vol. 57 (17), pp. 4727-4731. Date of Electronic Publication: 2018 Mar 15.
  • Publication Type:
    Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't
  • Language:
    English
  • Additional Information
    • Source:
      Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 0370543 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3773 (Electronic) Linking ISSN: 14337851 NLM ISO Abbreviation: Angew Chem Int Ed Engl Subsets: MEDLINE
    • Publication Information:
      Publication: <2004-> : Weinheim : Wiley-VCH
      Original Publication: Weinheim/Bergstr. : New York, : Verlag Chemie ; Academic Press, c1962-
    • Subject Terms:
      Copper/*chemistry ; Hydrocarbons, Iodinated/*chemistry ; Organophosphonates/*chemical synthesis ; Zinc/*chemistry; Alkylation ; Catalysis ; Molecular Structure ; Organophosphonates/chemistry ; Salts/chemistry ; Stereoisomerism
    • Abstract:
      α-Vinylation of phosphonates, phosphine oxides, sulfones, sulfonamides, and sulfoxides has been achieved by selective C-H zincation and copper-catalyzed C(sp 3 )-C(sp 2 ) cross-coupling reaction using vinylphenyliodonium salts. The vinylation transformation proceeds in high efficiency and stereospecificity under mild reaction conditions. This zincative cross-coupling reaction represents a general alkenylation strategy, which is also applicable for α-alkenylation of esters, amides, and nitriles in the synthesis of β,γ-unsaturated carbonyl compounds.
      (© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
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    • Grant Information:
      R01 GM118786 United States GM NIGMS NIH HHS
    • Contributed Indexing:
      Keywords: C(sp3)−H functionalization; copper catalysis; iodonium salt; vinylation
    • Accession Number:
      0 (Hydrocarbons, Iodinated)
      0 (Organophosphonates)
      0 (Salts)
      789U1901C5 (Copper)
      J41CSQ7QDS (Zinc)
    • Publication Date:
      Date Created: 20180227 Date Completed: 20190603 Latest Revision: 20190603
    • Publication Date:
      20240829
    • Accession Number:
      PMC6233314
    • Accession Number:
      10.1002/anie.201713278
    • Accession Number:
      29479782