Stereoselective Synthesis of (Z)-Perfluoroalkyl-1-iodo-1-triisopropyl Silylalkenes: A Convenient Route to Perfluoroalkyl-Substituted Unsaturated Synthons

Abstract

The quantitative and fully stereoselective synthesis of (Z)-perfluoroalkyl-1-iodo-1-triisopropylsilylalkenes and their easy, high-yielding transformation into the corresponding 1-iodo-2-perfluoroacetylenes and (Z)-2-perfluoroalkyl-1-iodo-1-alkenes, compounds of interest as synthons for classical organometallic chemistry or for metal-catalyzed coupling reactions, are discussed.

Keywords:

• Perfluoroacetylenes
• stereoselective synthesis
• (Z)-1-iodoperfluoroalkenes

ACKNOWLEDGMENT

Financial support for this work from the Ministerio de Educación y Ciencia (Spain), through project CTQ2006-15611-C02-02/BQU, is gratefully acknowledged.

Notes

^a Rf(n) = perfluorinated chain of n carbon atoms.

^b Calculated as isolated isomer mixture.

^c Calculated from the ¹H or ¹⁹F NMR spectra.