Utilization of the Stannyl Anionic Species Generated from Me3SiSnBu3 and X- in Organic Synthesis
- 1 March 1999
- journal article
- account
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1999 (3) , 269-280
- https://doi.org/10.1055/s-1999-2592
Abstract
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.Keywords
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