Synthesis and deprotonation of (phenylselenolatodimethylsilyl)bis(trimethylsilyl) methane: The crystal structure of (Me3Si)2(Me2SiBr)CH

The moisture-sensitive compound [{bromodimethylsilyl}bis(trimethylsilyl)methane], [(Me3Si)2(Me2SiBr)CH] 1 has been synthesized by the bromination of the hydride [(Me3Si)2(Me2SiH)CH] in CCl4 in good yield. Compound 1 has been characterized by multinuclear NMR and a single crystal X-ray diffraction studies. The average Si–C and BrMe2Si–C distances are, respectively, 1.894(2) and 1.886(2) Å. The Si–C–Si angle is 114.98(13)°. Treatment of 1 with NaSePh (obtained from the sodium triethylborohydride reduction of diphenyldiselenide) in benzene at room temperature resulted in the isolation of light yellow oil, [{phenylselenatodimethylsilyl}bis(trimethylsilyl)methane], [(Me3Si)2(Me2SiSePh)CH] 2. Compound 2 has been metallated with methyllithium as well as lithium diisopropylamide (LDA) in THF to give [(Me3Si)2(Me2SiSePh)CLi·2THF] 3. Compounds 2 and 3 have been characterized by elemental analysis, mass and multinuclear NMR studies.

► We synthesize and structurally characterize bromodimethylsilylbis(trimethylsilyl)methane.
► The bromide has been successfully converted into a bulky ligand with a potential selenium donor function.
► The selenium derivative is readily metallated to give lithium compound.
► The NMR study suggests that lithium compound exists as ion-pair in solution.