Trifluoromethylation of alkenyl bromides and iodides (including 5-iodouracils) with (CF3)2Hg and Cu ("trifluoromethylcopper")

J Org Chem. 2007 Mar 30;72(7):2678-81. doi: 10.1021/jo062544a. Epub 2007 Mar 3.

Abstract

Bromo- and iodoalkenes undergo trifluoromethylation efficiently in DMA with "CF3Cu" generated from (CF3)2Hg and Cu. Variable stereochemical inversion is observed with substrates having a gem-carbonyl group. Substrates having gem-hydrogen, -alkyl, or -alkenyl groups give products with stereochemical retention.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Bromides / chemistry*
  • Fluorine / chemistry*
  • Iodides / chemistry*
  • Methylation
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Uracil / chemistry*

Substances

  • Alkenes
  • Bromides
  • Iodides
  • Organometallic Compounds
  • trifluoromethylcopper
  • Fluorine
  • Uracil