Oxidative C-H bond functionalization and ring expansion with TMSCHN2 : a copper(I)-catalyzed approach to dibenzoxepines and dibenzoazepines

Angew Chem Int Ed Engl. 2015 Apr 20;54(17):5049-53. doi: 10.1002/anie.201411726. Epub 2015 Mar 3.

Abstract

Tricyclic dibenzoxepines and dibenzazepines are important therapeutic agents for the pharmaceutical industry and academic research. However, their syntheses are generally rather tedious, requiring several steps that involve a Wagner-Meerwein-type rearrangement under harsh conditions. Herein, we present the first copper(I)-catalyzed oxidative CH bond functionalization and ring expansion with TMSCHN2 to yield these important derivatives in a facile and straightforward way.

Keywords: CH functionalization; TMSCHN2; copper; heterocycles; ring expansion.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azepines / chemistry*
  • Carbon / chemistry
  • Catalysis
  • Coordination Complexes / chemistry
  • Copper / chemistry*
  • Diazomethane / analogs & derivatives*
  • Diazomethane / chemistry
  • Dibenzoxepins / chemistry
  • Hydrogen / chemistry
  • Oxidation-Reduction
  • Thermodynamics
  • Trimethylsilyl Compounds / chemistry*

Substances

  • Azepines
  • Coordination Complexes
  • Dibenzoxepins
  • Trimethylsilyl Compounds
  • Diazomethane
  • Carbon
  • Copper
  • Hydrogen
  • trimethylsilyldiazomethane