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Please login or sign up for a free trial to access the full content. Variation 4: Reaction of Organotellurenyl Halides and Derivatives with Alk-1-enyl Cuprates or Alk-1-enyl Mercury Derivatives

DOI: 10.1055/sos-SD-033-00396

Avilov, D.; Dittmer, D.Science of Synthesis, (200733311.

The cis-carbocupration of alkynyl sulfoxides 32[‌34‌,‌73‌] or alkynylphosphine oxides 34[‌74‌,‌75‌] followed by reaction with benzenetellurenyl iodide yields 1-(phenyltellanyl)alk-1-enyl sulfoxides 33 (3485%) and [1-(phenyltellanyl)alk-1-enyl]phosphine oxides 35 (7480%), respectively, in a regio- and stereoselective fashion (Scheme 12). A corresponding reaction of ethyl 3-phenylprop-2-ynoate (36, R1=Ph) with an organocuprate [MeCu(CN)Li] yields an E/Z-isomeric mixture of alk-1-enyl tellurides, but the reactions of other ethyl propynoates 36 with various organocuprates gives alk-1-enyl tellurides 37 as a single isomer in 4070% yields.[‌76‌]

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