Stereoselective Synthesis of Internal Alkenyl Iodides from Alkynes via Addition  of Hydrogen Iodide Generated in situ from a Chlorotrimethylsilane/Sodium  Iodide/Water System

Naoshi Kamiya; Yoshihiro Chikami; Yasutaka Ishii

doi:10.1055/s-1990-21207

Synlett 1990; 1990(11): 675-676
DOI: 10.1055/s-1990-21207

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Stereoselective Synthesis of Internal Alkenyl Iodides from Alkynes via Addition of Hydrogen Iodide Generated in situ from a Chlorotrimethylsilane/Sodium Iodide/Water System

Naoshi Kamiya^* , Yoshihiro Chikami, Yasutaka Ishii

^*Department of Applied Chemistry, Kansai University, Suita, Osaka 564, Japan

Abstract

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Hydrogen iodide, cleanly generated in situ from chlorotrimethylsilane/sodium iodide/water in acetonitrile under mild conditions, was found to be an attractive reagent for the synthesis of alkenyl iodides. The hydrogen iodide thus generated added to both terminal and internal alkynes with complete cis-selectivity in a Markovnikov fashion to give the corresponding (E)-alkenyl iodides in fair to good yield.

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