Synthesis of 3-Silylated 3-Sulfolenes from Propargylsilanes and their Reductive Desulfitation

Chemistry of Heterocyclic Compounds 2021
Rūdolfs Beļaunieks, Mikus Puriņš, Viktors Kumpiņš, Māris Turks

[Figure not available: see fulltext.] Protonation of propargylsilanes induces 1,2-silyl group shift and provides 2-silylated dienes. If this reaction is performed in liquid SO2, the diene formation is followed by instant cheletropic SO2 addition, and 3-silylated 3-sulfolenes are obtained. Liquid SO2 as polar and Lewis acidic reaction medium makes it possible to use relatively weak Brønsted acid catalysts such as H2O and benzoic acid. Depending on the starting material, reductive desulfitation of 3-silylated 3-sulfolenes provides vinyl, allyl, or aliphatic silanes.

Keywords
1,2-silyl migration | cheletropic addition | desulfitation | propargylsilanes | silyl sulfolenes
DOI
10.1007/s10593-021-02862-1
Hyperlink
https://link.springer.com/article/10.1007%2Fs10593-021-02862-1

Beļaunieks, R., Puriņš, M., Kumpiņš, V., Turks, M. Synthesis of 3-Silylated 3-Sulfolenes from Propargylsilanes and their Reductive Desulfitation. Chemistry of Heterocyclic Compounds, 2021, Vol. 57, No. 1, pp.20-25. ISSN 0009-3122. Available from: doi:10.1007/s10593-021-02862-1

Publication language
English (en)