Copper-catalyzed trifluoromethylation of trisubstituted allylic and homoallylic alcohols

Chemistry. 2015 Apr 27;21(18):6700-3. doi: 10.1002/chem.201406627. Epub 2015 Mar 24.

Abstract

An efficient copper-catalyzed trifluoromethylation of trisubstituted allylic and homoallylic alcohols with Togni's reagent has been developed. This strategy, accompanied by a double-bond migration, leads to various branched CF3-substituted alcohols by using readily available trisubstituted cyclic/acyclic alcohols as substrates. Moreover, for alcohols in which β-H elimination is prohibited, CF3-containing oxetanes are isolated as the sole product.

Keywords: (homo)allylic alcohols; branched products; copper; radical reactions; trifluoromethylation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Chlorofluorocarbons, Methane / chemistry*
  • Copper / chemistry*
  • Ethers, Cyclic / chemical synthesis*
  • Ethers, Cyclic / chemistry
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Methylation
  • Molecular Structure
  • Propanols / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Chlorofluorocarbons, Methane
  • Ethers, Cyclic
  • Heterocyclic Compounds
  • Propanols
  • allyl alcohol
  • Copper
  • fluoroform