One, Two, Three, Go: Novel Applications of 1,2-Silyl Shift for 1,3-Difunctionalization of Propargyl Silanes

Balticum Organicum Syntheticum 2024: Abstract Book 2024
Māris Turks, Rasma Kroņkalne, Artjoms Ubaidullajevs, Rūdolfs Beļaunieks, Armands Sebris, Mikus Puriņš, Raimonds Rogaļevs

Propargyl silanes can act as precursors of 1,3-dipols, if their electrophilic activation is followed by 1,2-silyl shift. Herein, we report propargyl silane 1 activation by electrophiles (H+, X+, RSe+, R-Cu(III)) that results in allyl cation 3 formation. The latter is trapped with various N-, O-, S-, C-nucleophiles in either intramolecular or intermolecular fassion. This provides higly 1,2,3-functionalized systems 4, 5, 6 with possibilities for further derivatization.

Keywords
1,2-Silyl Shift, Propargyl Silanes, 1,3-Functionalization

Turks, M., Kroņkalne, R., Ubaidullajevs, A., Beļaunieks, R., Sebris, A., Puriņš, M., Rogaļevs, R. One, Two, Three, Go: Novel Applications of 1,2-Silyl Shift for 1,3-Difunctionalization of Propargyl Silanes. In: Balticum Organicum Syntheticum 2024: Abstract Book, Latvia, Riga, 7-10 July, 2024. Riga: 2024, pp.156-156.

Publication language
English (en)