Abstract
The one-pot multistep ethyltellurenylation reaction of epoxides with elemental tellurium and lithium triethylborohydride is described. The reaction mechanism was experimentally investigated. Dilithium ditelluride and triethyl borane, formed from elemental tellurium and lithium triethylborohydride, were shown to be the key species involved in the reaction mechanism. Epoxides undergo ring-opening reaction with dilithium ditelluride to afford β-hydroxy ditellurides, which are sequentially converted into the corresponding β-hydroxy-alkyl ethyl tellurides by transmetalation with triethyl borane, reasonably proceeding through the SH2 mechanism.
Highlights
Organoselenium [1,2] and organotellurium [3] compounds continue to find wide application in chemical sciences and biology [4,5,6,7,8]
Part ofa our growing interest in of theanstudy of the reaction chemistry organotellurium compounds,aswea report study on the mechanism unexpected of of organotellurium compounds, we report a study on the mechanism of antounexpected reaction epoxides with elemental tellurium and lithium triethylborohydride, leading the formation of β- of epoxides with elemental tellurium and lithium triethylborohydride, leading to the formation of hydroxy-alkyl ethyl tellurides
We initially evaluated whether tris(ethyltelluro)borane 4 could be generated upon the treatment of of elemental tellurium with lithium triethylborohydride
Summary
Organoselenium [1,2] and organotellurium [3] compounds continue to find wide application in chemical sciences and biology [4,5,6,7,8]. Tellurium-containing derivatives play an important role in organic synthesis [3,9], materials science [10,11], and medicinal chemistry [8,12,13,14,15]. Often undergoing regio- and stereo-selective transformations, organotellurium compounds can be employed in synthetically useful functional group conversion reactions [26,27] and carbon-carbon bond-forming processes [28,29,30,31]. Owing to these features, tellurenylation reactions provide an attractive functional handle for further elaboration. Selected examples of biological and synthetic applications of organotellurium compounds are presented in the Figure 1
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