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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

A Reverse Wittig Coupling with Trifluoroacetaldehyde: A Convenient One-Step Synthesis of Trifluoromethyl Alkenes

Author(s): Shainaz M. Landge, Dmitry A. Borkin and Bela Torok

Volume 6, Issue 6, 2009

Page: [439 - 443] Pages: 5

DOI: 10.2174/157017809789124795

Price: $65

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.

Keywords: Trifluoroacetaldehyde ethyl hemiacetal, fluoral, witting coupling, aryl-α-trifluoromethyl-alkenes


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