<p>A series of cationic acetylacetonate palladium complexes bearing phosphine and diphosphine ligands have been tested in combination with BF<sub>3</sub>⋅OEt<sub>2</sub> for the N‑allylation of secondary aliphatic amines using allylic alcohol as the alkylating agent. Catalyst screening and optimization have determined the superior activity of the catalyst system [Pd(acac)(dppf)]BF4/<i>n</i>BF<sub>3</sub>⋅OEt<sub>2</sub> (dppf – 1,1′-bis(diphenylphosphino)ferrocene) for N‑allylation of morpholine with allyl alcohol in the presence of 3Å molecular sieves (TON up to 35 000).</p> Graphical Abstract <p></p>

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N-allylation of Amines with Allyl Alcohol Catalyzed by Cationic Acetylacetonate Palladium Complexes Bearing Phosphine Ligands

  • Zorikto D. Abramov,
  • Ivan D. Oreshkin,
  • Timur S. Orlov,
  • Mikhail V. Bykov,
  • Dmitry S. Suslov

摘要

A series of cationic acetylacetonate palladium complexes bearing phosphine and diphosphine ligands have been tested in combination with BF3⋅OEt2 for the N‑allylation of secondary aliphatic amines using allylic alcohol as the alkylating agent. Catalyst screening and optimization have determined the superior activity of the catalyst system [Pd(acac)(dppf)]BF4/nBF3⋅OEt2 (dppf – 1,1′-bis(diphenylphosphino)ferrocene) for N‑allylation of morpholine with allyl alcohol in the presence of 3Å molecular sieves (TON up to 35 000).

Graphical Abstract