Synthesis of Highly Functionalized Alkenes from Propargyl Silanes via 1,2-Silyl Migration

Stereoselective Alkene Functionalizations: Beilstein Organic Chemistry Symposium 2022 2022
Rūdolfs Beļaunieks, Mikus Puriņš, Rasma Kroņkalne, Rebeka Anna Līpiņa, Artjoms Ubaidullajevs, Māris Turks

Stabilizing properties of -silicon effect has been known to increase the rate of the reactions for unsaturated systems that proceed via the formation of -silyl carbenium ion. The effect can be achieved by either vertical (hyperconjugation) or non-vertical (formation of cyclic silonium ion) stabilization. The formation of the latter in the combination with other stabilizing effects can lead the reactions to proceed via 1,2-silyl migration [1]. Recently, we have reported the use of Brønsted acids as the catalyst for the synthesis of silyldienes and indenes from propargylsilanes [2,3].

Keywords
Alkene, alkyne, propargyl silane, beta-silly migration

Beļaunieks, R., Puriņš, M., Kroņkalne, R., Līpiņa, R., Ubaidullajevs, A., Turks, M. Synthesis of Highly Functionalized Alkenes from Propargyl Silanes via 1,2-Silyl Migration. In: Stereoselective Alkene Functionalizations: Beilstein Organic Chemistry Symposium 2022, Germany, Ruedesheim am Rhein, 26-28 April, 2022. Ruedesheim: Beilstein Institut, 2022, pp.32-32.

Publication language
English (en)