Palladium-Catalyzed Aminocarbonylation of Allylic Alcohols

Haoquan Li, Helfried Neumann, Matthias Beller

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

A benign and efficient palladium-catalyzed aminocarbonylation reaction of allylic alcohols is presented. The generality of this novel process is demonstrated by the synthesis of β,γ-unsaturated amides including aliphatic, cinnamyl, and terpene derivatives. The choice of ligand is crucial for optimal carbonylation processes: Whereas in most cases the combination of PdCl2with Xantphos (L6) gave best results, sterically hindered substrates performed better in the presence of simple triphenylphosphine (L10), and primary anilines gave the best results using cataCXium® PCy (L8). The reactivity of the respective catalyst system is significantly enhanced by addition of small amounts of water. Mechanistic studies and control experiments revealed a tandem allylic alcohol amination/C−N bond carbonylation reaction sequence.

Original languageEnglish
Pages (from-to)10050-10056
Number of pages7
JournalChemistry - A European Journal
Volume22
Issue number29
DOIs
StatePublished - 11 Jul 2016
Externally publishedYes

Keywords

  • allylic
  • amide
  • carbonylation
  • homogeneous catalysis
  • palladium

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