S(N)2' reaction of allylic difluorides with lithium amides and thiolates

Org Lett. 2012 Dec 7;14(23):5888-91. doi: 10.1021/ol302802r. Epub 2012 Nov 12.

Abstract

The synthesis of monofluoroalkenes using an S(N)2' reaction of lithium amides derived from aromatic amines or lithium thiolates with 3,3-difluoropropenes is reported. This transformation features the use of fluoride as a leaving group.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis*
  • Alkenes / chemistry*
  • Amides / chemistry*
  • Combinatorial Chemistry Techniques
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry*
  • Lithium / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Sulfhydryl Compounds / chemistry*

Substances

  • Alkenes
  • Amides
  • Hydrocarbons, Fluorinated
  • Organometallic Compounds
  • Sulfhydryl Compounds
  • Lithium