Fluoroalkylcopper(I) complexes generated by the carbocupration of tetrafluoroethylene: construction of a tetrafluoroethylene-bridging structure

J Am Chem Soc. 2014 Oct 29;136(43):15158-61. doi: 10.1021/ja5093776. Epub 2014 Oct 20.

Abstract

We report a copper-mediated synthesis of a variety of 1,2-difunctionalized-1,1,2,2-tetrafluoroethylene derivatives via the carbocupration of tetrafluoroethylene. The key synthetic intermediates, 2-aryl-1,1,2,2-tetrafluoroethylcopper complexes, can be easily prepared, stored, and used as fluoroalkylation reagents. The molecular structure was unambiguously determined by X-ray crystallography and NMR analysis. We applied this method to the short-step synthesis of a liquid-crystalline compound bearing a tetrafluoroethylene-bridging structure.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Copper / chemistry*
  • Fluorocarbons / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Organometallic Compounds / chemistry*

Substances

  • Fluorocarbons
  • Organometallic Compounds
  • Copper
  • tetrafluoroethylene