BTMSA is used as a
nucleophile in
Friedel-Crafts type
acylations and
alkylations and a precursor to lithium trimethylsilylacetylide. The TMS groups can be removed with
tetra-n-butylammonium fluoride (TBAF) and replaced with protons. BTMSA is also a useful
reagent in
cycloaddition reactions. Illustrating its versatility, BTMSA was used in a concise total synthesis of (±)-
estrone. A key step in this synthesis was the formation of the steroidal skeleton, catalyzed by
CpCo(CO)2. BTMSA also serves as a
ligand in
organometallic chemistry. For example, it forms stable
adducts with
metallocenes. : Cp2TiCl2 + Mg + Me3SiC≡CSiMe3 → Cp2Ti(η²-Me3SiC₂SiMe3) + MgCl2 == References ==