Samarium (II) diiodide‐induced reductive cleavage of SeSe and TeTe bond in diphenyl diselenide and ditelluride leading to a samarium phenylselenolate and tellurolate: Preparation of unsymmetrical alkylphenyl selenides and tellurides

Abstract

AbstractDiphenyl diselenide and diphenyl ditelluride were reduced by samarium (II) diiodide in tetrahydrofuran‐hexamethylphosphoric triamide to produce samarium phenylselenolate and samarium phenyltellurolate, respectively. This new selenolate or tellurolate anion species reacted smoothly with alkyl, allyl, and benzyl halides to give alkyl‐, allyl‐, and benzylphenyl selenides or tellurides in good yields under mild and neutral conditions. The samarium selenolate reacted with α‐halo ketones to give the corresponding α‐phenylseleno ketones. 1,4‐Addition with α,β‐enones proceeded to give 3‐phenylseleno ketones in moderate yields. Isolation of phenylselenotributyltin or phenylseleno‐trimethylsilane by transmetalation with tributyltin iodide or trimethylchlorosilane, respectively, suggested the presence of the samarium selenolate species.