Utilization of the Stannyl Anionic Species Generated from Me₃SiSnBu₃ and X^- in Organic Synthesis

The stannyl anionic species, generated from Me₃SiSnBu₃ and R₄NX, CsF or TASF [(Et₂N)₃S⁺SiMe₃F₂ ^-], is an interesting and useful reagent in organic synthesis. This anionic species can be used for the halogen-metal exchange reaction, generating an aryl or vinyl anion. Thus a novel cyclization of aryl or vinyl halides bearing a carbonyl group in a tether was developed. On the other hand, reactive intermediates such as carbene, benzyne, and quinodimethane could be generated by 1,1-, 1,2-, or 1,4-eliminations from the corresponding dihalogenated compounds. The Michael addition of the stannyl anionic species to methyl propiolate gave methyl bis-stannyl propionate in high yield and this is a useful synthon in organic synthesis.

tributylstannyltrimethylsilane - silylstannane - stannyl anion - o-quinodimethane - bisstannylated compound