Approach to vicinal t-Boc-amino dibromides via catalytic aminobromination of nitrostyrenes without using chromatography and recrystallization

J Org Chem. 2013 Feb 1;78(3):1171-5. doi: 10.1021/jo302727v. Epub 2013 Jan 23.

Abstract

A 1.0 mol % amount of K(3)PO(4)·3H(2)O was found to catalyze aminohalogenation reaction of nitrostyrenes with N,N-dibromo-tert-butylcarbamate (t-Boc-NBr(2)) in a dichloroethane system. Good to excellent yields and complete regioselectivity have been achieved by taking advantage of the GAP workup without using traditional purification techniques such as column chromatography and recrystallization. Anew mechanism is proposed involving radical and ionic catalytic cycles and an intramolecular migration.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Formamides / chemical synthesis*
  • Formamides / chemistry
  • Halogenation
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nitro Compounds / chemical synthesis
  • Nitro Compounds / chemistry*
  • Stereoisomerism
  • Styrenes / chemistry*

Substances

  • 1-(tert-butoxyformamido)-2,2-dibromo-1-phenyl-2-nitroethane
  • Formamides
  • Nitro Compounds
  • Styrenes