Pd(0)-catalyzed sequential C-N bond formation via allylic and aromatic C-H amination of α-methylstyrenes with diaziridinone

Org Lett. 2013 Aug 16;15(16):4210-3. doi: 10.1021/ol401935c. Epub 2013 Aug 6.

Abstract

A novel Pd(0)-catalyzed sequential C-N bond formation process via allylic and aromatic C-H amination of α-methylstyrenes with di-tert-butyldiaziridinone, giving spirocyclic indolines in good yields, is described. Four C-N bonds and one spiro quaternary carbon are generated in a single operation.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Amination
  • Aziridines / chemistry*
  • Catalysis
  • Hydrogen Bonding
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure
  • Palladium / chemistry*
  • Styrenes / chemistry*

Substances

  • Aziridines
  • Indoles
  • Styrenes
  • di-tert-butyldiaziridinone
  • vinyltoluene
  • Palladium