Organotellurium Chemistry - Applications - Organic Synthesis

Organic Synthesis

Diphenyl ditelluride is used as a source of PhTe- in organic synthesis. Some of its reactions are:

  • Organic reduction of aldehydes, alkenes, alkynes, nitro compounds, oxiranes to alkenes
  • Debromination of vicinal dibromides with E2 elimination

Other methods in organotellurium chemistry include:

  • Tellurium in vinylic tellurium trichlorides can be replaced by halides with a variety of reagents (iodine, NBS)
  • Detellurative cross-coupling reaction: Compounds of the type Ar2TeCl2 engage in a coupling reaction to the corresponding biaryls with Raney nickel or palladium
Another type is this Stille reaction:
  • Hydrotelluration: Compounds of the type RTeH react with alkynes R'CCH to R'HCCTeR with anti addition to a Z-alkene. In contrast hydrostannylation, hydrozirconation and hydroalumination in similar reactions react with syn addition.
  • Te/Li exchange in transmetallation is used in the synthesis of lithium reagents with demanding functional groups.
  • Allylic oxidation: like the selenium counterpart selenoxide oxidation, allylic telluroxides undergo -sigmatropic rearrangements forming allylic alcohols after hydrolysis.
  • Olefin synthesis: Like the selenium counterpart selenoxide elimination, certain telluroxides (RTeOR) can form alkenes on heating.

Read more about this topic:  Organotellurium Chemistry, Applications

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