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Generating Active “L-Pd(0)” via Neutral or Cationic π‑Allylpalladium Complexes Featuring Biaryl/Bipyrazolylphosphines: Synthetic, Mechanistic, and Structure–Activity Studies in Challenging Cross-Coupling Reactions

DeAngelis, A. J ; Gildner, Peter G ; Chow, Ruishan ; Colacot, Thomas J

Journal of organic chemistry, 2015-07, Vol.80 (13), p.6794-6813 [Periódico revisado por pares]

United States: American Chemical Society

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  • Título:
    Generating Active “L-Pd(0)” via Neutral or Cationic π‑Allylpalladium Complexes Featuring Biaryl/Bipyrazolylphosphines: Synthetic, Mechanistic, and Structure–Activity Studies in Challenging Cross-Coupling Reactions
  • Autor: DeAngelis, A. J ; Gildner, Peter G ; Chow, Ruishan ; Colacot, Thomas J
  • É parte de: Journal of organic chemistry, 2015-07, Vol.80 (13), p.6794-6813
  • Notas: ObjectType-Article-1
    SourceType-Scholarly Journals-1
    ObjectType-Feature-2
    content type line 23
  • Descrição: Two new classes of highly active yet air- and moisture-stable π-R-allylpalladium complexes containing bulky biaryl- and bipyrazolylphosphines with extremely broad ligand scope have been developed. Neutral π-allylpalladium complexes incorporated a range of biaryl/bipyrazolylphosphine ligands, while extremely bulky ligands were accommodated by a cationic scaffold. These complexes are easily activated under mild conditions and are efficient for a wide array of challenging C–C and C–X (X = heteroatom) cross-coupling reactions. Their high activity is correlated to their facile activation to a 12-electron-based “L-Pd(0)” catalyst under commonly employed conditions for cross-coupling reactions, noninhibitory byproduct release upon activation, and suppression of the off-cycle pathway to form dinuclear (μ-allyl)­(μ-Cl)­Pd2(L)2 species, supported by structural (single crystal X-ray) and kinetic studies. A broad scope of C–C and C–X coupling reactions with low catalyst loadings and short reaction times highlight the versatility and practicality of these catalysts in organic synthesis.
  • Editor: United States: American Chemical Society
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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