The C-H activation/1,3-diyne strategy: highly selective direct synthesis of diverse bisheterocycles by Rh(III) catalysis

Angew Chem Int Ed Engl. 2014 Sep 1;53(36):9650-4. doi: 10.1002/anie.201403782. Epub 2014 Jul 1.

Abstract

The reactivity and selectivity of 1,3-diynes in transition-metal-catalyzed CH activation is exploited to quickly assemble diverse polysubstituted bisheterocycles, which are highly important but difficult to access. By using the CH activation/1,3-diyne strategy, we overcame the challenges of selectivity (chemo-, regio-, and mono-/diannulation) and constructed seven kinds of adjacent bisheterocycles through the formation of four strategic bonds with high efficiency and high selectivity.

Keywords: CH activation; RhIII catalysis; alkynes; heterocycles; selectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Catalysis
  • Isoquinolines / chemical synthesis
  • Isoquinolines / chemistry
  • Pyridines / chemistry
  • Rhodium / chemistry*
  • X-Ray Diffraction

Substances

  • Bridged Bicyclo Compounds, Heterocyclic
  • Isoquinolines
  • Pyridines
  • Rhodium