An Efficient Protocol to Synthesize N-Acyl-enamides and -Imines by Pd-Catalyzed Carbonylations

Lin Wang, Helfried Neumann, Anke Spannenberg, Matthias Beller

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

For the first time, the bidentate phosphinite ligand 1,2-bis(di-tert-butylphosphinoxy)ethane (tBu2POCH2CH2OPtBu2) was synthesized. In the presence of this ligand, various N-acyl enamides were obtained in good yields and chemoselectivity by Pd-catalyzed carbonylation reaction of imines containing α-H. Meanwhile, imines without α-H could be transformed to N-acyl imines, which form highly hindered amides by straightforward addition of Grignard reagents.

Original languageEnglish
Pages (from-to)2164-2172
Number of pages9
JournalChemistry - A European Journal
Volume24
Issue number9
DOIs
StatePublished - 9 Feb 2018
Externally publishedYes

Keywords

  • 1,2-bis(di-tert-butylphosphinoxy)ethane
  • carbon monoxide
  • enamides
  • homogeneous catalysis
  • imines
  • palladium

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