Abstract
Studies on organotellurium compounds have not been extensively conducted due to a lack of tolerable synthetic methods, difficult isolation processes, and their chemical instabilities. Overcoming these hurdles, we developed an efficient and mild method for the selective synthesis of symmetrical diorganyl tellurides 1, a representative class of organotellurium compounds, using a proper reducing reagent. The reaction condition was optimized for the selective formation of 1 by forming the telluride dianion (Te(2-)) using a reducing reagent, sodium borohydride (NaBH(4)), and then followed by the addition of organyl halides. The optimized reaction condition was as follows: (1) Te (1.0 eq), NaBH(4) (2.5 eq) in DMF for 1 h at 80 °C; (2) organyl halides (2.0 eq) for 3-5 h at 25-153 °C. Using this condition, 18 various diorganyl tellurides 1 were selectively and efficiently synthesized in reasonable yields (37-93%). The reaction pathways for the formation of diorganyl tellurides 1 were also investigated. Consequently, we established a practical and efficient method for the selective synthesis of diorganyl tellurides 1 as a representative class of organotellurium compounds.