4.8 Article

Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles

Journal

CHEMICAL SCIENCE
Volume 10, Issue 12, Pages 3632-3636

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc05689g

Keywords

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Funding

  1. National Key R&D Program of China [2017YFA0700103]
  2. NSFC [21502191, 21672213, 21871258]
  3. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  4. Haixi Institute of CAS [CXZX-2017-P01]

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Classical 1,4-dicarbofunctionalization of 1,3-enynes employs organometallic reagents as nucleophiles to initiate the reaction. We report a copper-catalyzed 1,4-alkylarylation of 1,3-enynes with alkyl diacyl peroxides as masked alkyl electrophiles and aryl boronic acids as nucleophiles, selectively affording structurally diversified tetrasubstituted allenes under mild conditions. Mechanistic studies suggest that an allenyl radical might be involved.

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