Fluorous synthesis of allylic fluorides: C-F bond formation as the detagging process

Chem Commun (Camb). 2008 Aug 21:(31):3622-4. doi: 10.1039/b804484h. Epub 2008 Jun 4.

Abstract

A novel fluorous tagging-detagging strategy has been developed featuring a fluorination as the detagging process; fluorous allylsilanes were prepared by cross-metathesis and subsequently subjected to electrophilic fluorodesilylation; Selectfluor was used as the detagging reagent; the resulting allylic fluorides were successfully purified by fluorous solid phase extraction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis*
  • Alkenes / chemistry
  • Alkenes / isolation & purification
  • Catalysis
  • Fluorides / chemistry*
  • Halogenation
  • Silanes / chemical synthesis*
  • Silanes / chemistry
  • Silanes / isolation & purification
  • Solid Phase Extraction

Substances

  • Alkenes
  • Silanes
  • allylsilane
  • Fluorides