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BTMSA is used as starting reagent in the synthesis of functionalized 4-R-1,2-bis(trimethylsilyl)benzenes. It is also used in the synthesis of (+)-brasilenyne2 and (β-diketanato)Ag(BTMSA). Bis(trimethylsilyl)acetylene is a ligand that binds to a central metal ion (e.g. Titanium) to create a coordination complex. One of its complexes, Permethyltitanocene-bis(trimethylsilyl)acetylene, is a catalyst for the head-to-tail dimerization of 1-alkynes (e.g. 3-Penten-1-yne [P227430]).
Christian Reus.; Liu NW.; Bolte M.; Lerner HW.; Wagner M. Synthesis of bromo-, boryl-, and stannyl-functionalized 1,2-bis(trimethylsilyl)benzenes via Diels-Alder or C-H activation reactions.J. Org. Chem.,2012,77(7), 3518-3523.
Denmark SE.; Yang SM. Intramolecular silicon-assisted cross-coupling: total synthesis of (+)-brasilenyne.J Am Chem Soc.,2002,124(51), 15196-15197.
Akinobu Horita.; Hayato Tsurugi.; Tetsuya Satoh.; Masahiro Miura. IRhodium-catalyzed anti selective cross-addition of bis(trimethylsilyl)acetylene to diarylacetylenes via carbon-silicon bond cleavage.Org Lett.,2008,10(9), 1751-1754.
Reacts with electrophiles via Si-stabilized carbocations ions and subsequent desilylation; see Appendix 4. Thus, Lewis acid promoted reaction with acid chlorides gives alkynyl ketones, leading to a synthesis of ɑß-enals: J. Org. Chem., 38, 2254 (1973); 57, 3203 (1992):
Addition to chiral acetals in the presence of TiCl4 leads to ɑ-hydroxy alkynes in high yield and ee: J. Am . Chem. Soc., 105, 2904 (1983); J. Chem. Soc., Perkin 1, 3301 (1991). Sulfonyl chlorides give alkynyl sulfones: Org. Synth. Coll., 8, 281 (1993), and references therein.
Precursor of lithium TMS acetylide: J. Chem. Soc., Chem. Commun., 840 (1979), and dilithioacetylide: Tetrahedron Lett., 34, 839 (1993).
Gefahrenhinweise (EU): H226
Flammable liquid and vapour.
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