4.5 Article

Copper-Catalyzed Silylcupration of Activated Alkynes

Journal

SYNTHESIS-STUTTGART
Volume 48, Issue 19, Pages 3373-3381

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0035-1562460

Keywords

copper catalysis; silylcupration; ynamides; propiolates; silylboronates

Funding

  1. Universite Catholique de Louvain
  2. Universite libre de Bruxelles (ULB)
  3. Universite de Versailles Saint-Quentin-en-Yvelines
  4. Fonds pour la formation a la Recherche dans l'Industrie et dans l'Agriculture (F.R.I.A.)
  5. Ministere de la Recherche

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A highly efficient catalytic silylcupration of activated alkynes is reported. Upon reaction with silylboronates and methanol in THF at room temperature in the presence of copper(I) fluoride tris(triphenylphosphine), a range of ynamides and propiolates were found to undergo a smooth silylcupration. This reaction, which tolerates various functional groups, affords a straightforward and efficient entry to the corresponding beta-silylenamides and -acrylates, which were formed with high levels of regio-and stereoselectivities.

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