A Reverse Wittig Coupling with Trifluoroacetaldehyde: A convenient one-step synthesis of Trifluoromethyl Alkenes

Shainaz M. Landge, Dmitry A. Borkin, Béla Török

Research output: Contribution to journalArticlepeer-review

Abstract

A novel, mild synthesis of aryl-3,3,3-trifluoropropenes by Wittig olefination of benzylphosphonium ylides with in-situ generated trifluoroacetaldehyde is described. The in-situ formed trifluoroacetaldehyde efficiently traps the Wittig ylides and yields trifluoromethyl alkenes without the troublesome handling. The scope of the reaction was tested in reaction of trifluoroacetaldehyde with a wide variety of benzylphosphonium ylides. The α-trifluoromethyl alkenes were isolated in good to excellent yields in a convenient one step process.
Original languageAmerican English
JournalThe Journal of Organic Chemistry
Volume6
StatePublished - 2009

Keywords

  • Trifluoroacetaldehyde ethyl hemiacetal
  • aryl-α-trifluoromethyl-alkenes
  • fluoral
  • witting coupling

DC Disciplines

  • Chemistry

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