Expanding the Possibilities for Heterocycle Synthesis by Propargyl Silane Cyclization via the 1,2-Silyl Shift

Balticum Organicum Syntheticum 2024: Abstract Book 2024
Rasma Kroņkalne, Artjoms Ubaidullajevs, Rūdolfs Beļaunieks, Māris Turks

In this work we demonstrate the use propargyl silanes as precursors for various O-, S-, N-heterocycles, containing a highly stereodefined olefin side chain (Scheme 1). Brønsted acids, electrophilic halogen sources and selenyl chloride induce this transformation, providing diverse functionalization for the resulting olefin side chain. Further synthetic utility of the obtained products is demonstrated by electrophilic substitution (C=C-Si → C=C-Hal) and cross-coupling reactions.1 References 1. Kroņkalne, R.; Beļaunieks, R.; Ubaidullajevs, A.; Mishnev, A.; Turks, M. J. Org. Chem. 2023, 88, 13857.

Keywords
PROPARGYL SILANES, HETEROCYCLIZATION

Kroņkalne, R., Ubaidullajevs, A., Beļaunieks, R., Turks, M. Expanding the Possibilities for Heterocycle Synthesis by Propargyl Silane Cyclization via the 1,2-Silyl Shift. In: Balticum Organicum Syntheticum 2024: Abstract Book, Latvia, Riga, 7-10 July, 2024. Riga: 2024, pp.79-79.

Publication language
English (en)