Palladium-Catalyzed Direct Cyclopropylation of Heterocycles

Angew Chem Int Ed Engl. 2015 Aug 10;54(33):9601-5. doi: 10.1002/anie.201504735. Epub 2015 Jul 15.

Abstract

Many 1,3-azoles and thiophenes are directly cyclopropylated in the presence of a simple palladium catalyst. The relative configuration on the three-membered rings is retained in the products. Thus, the cyclopropyl-halide bond undergoes concerted oxidative addition to palladium(0) and cyclopropyl radicals are not involved in the productive pathway.

Keywords: alkyl halides; cyclopropane; heterocycles; palladium; synthetic methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azoles / chemical synthesis
  • Azoles / chemistry
  • Benzoxazoles / chemical synthesis
  • Benzoxazoles / chemistry
  • Catalysis
  • Cyclopropanes / chemical synthesis
  • Cyclopropanes / chemistry*
  • Heterocyclic Compounds / chemical synthesis
  • Heterocyclic Compounds / chemistry*
  • Iodides / chemical synthesis
  • Iodides / chemistry
  • Palladium / chemistry*
  • Thiophenes / chemical synthesis
  • Thiophenes / chemistry

Substances

  • Azoles
  • Benzoxazoles
  • Cyclopropanes
  • Heterocyclic Compounds
  • Iodides
  • Thiophenes
  • Palladium
  • cyclopropane