Rate and Computational Studies for Pd-NHC-Catalyzed Amination with Primary Alkylamines and Secondary Anilines: Rationalizing Selectivity for Monoarylation versus Diarylation with NHC Ligands

Christopher Lombardi, Richard P. Rucker, Robert D.J. Froese, Sepideh Sharif, Pier Alexandre Champagne, Michael G. Organ

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

The relative rates of arylation of primary alkylamines with different Pd-NHC catalysts have been measured, as have the relative rates of arylation of the secondary aniline product in an attempt to understand the key ligand design features necessary to have high selectivity for the monoarylated amine product. As the substituents on the N-aryl ring of the NHC increase in size, selectivity for monoarylation increases and this is further enhanced by chlorinating the back of the NHC ring. Computations have been performed on the catalytic cycle of this transformation in order to understand the selectivity obtained with the different catalysts.

Original languageEnglish (US)
Pages (from-to)14223-14229
Number of pages7
JournalChemistry - A European Journal
Volume25
Issue number62
DOIs
StatePublished - Nov 7 2019

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Keywords

  • PEPPSI
  • amination
  • catalysis
  • cross-coupling
  • rate study
  • selective

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