Rapid synthesis of fused N-heterocycles by transition-metal-free electrophilic amination of arene C-H bonds

Angew Chem Int Ed Engl. 2014 Mar 3;53(10):2701-5. doi: 10.1002/anie.201309973. Epub 2014 Jan 30.

Abstract

We disclose an efficient and operationally simple protocol for the preparation of fused N-heterocycles starting from readily available 2-nitrobiaryls and PhMgBr under mild conditions. More than two dozen N-heterocycles, including two bioactive natural products, have been synthesized using this method. A stepwise electrophilic aromatic cyclization mechanism was proposed by DFT calculations.

Keywords: N-heterocycles; carbazoles; electrophilic amination; nitrobiaryls; regioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Cyclization
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Quantum Theory

Substances

  • Heterocyclic Compounds
  • Organometallic Compounds