4.5 Article

A Simplified Protocol for the Stereospecific Nickel-Catalyzed C-S Vinylation Using NiX2 Salts and Alkyl Phosphites

Journal

SYNTHESIS-STUTTGART
Volume 52, Issue 2, Pages 311-319

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1690717

Keywords

nickel; cross-coupling; scalable; heterocycles

Funding

  1. University of Toronto (UofT)
  2. Natural Science and Engineering Research Council (NSERC)
  3. Alphora Research Inc.
  4. Kennarshore Inc.

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A Ni-catalyzed C-S cross-coupling using only NiI2 (0.5-2.5 mol%) and P(OiPr)(3) (2.0-10.0 mol%) is reported. Using an air-stable Ni(II) precatalyst, and a cheap and commercially available ligand, a scalable and robust method was developed to cross-couple various thiophenols and styryl bromides, including some sterically encumbered thiols, an alpha-bromocinnamaldehyde as well as a thiolation-cyclization.

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