The efficient method for the preparation of alkenylsilanes from organoaluminums

•Silyl esters of sulfonic acids are efficient silylating agents for alkenylaluminums.•The reaction proceeds in mild conditions to give alkenylsilanes in high yield.•The reaction with alumina cycles takes place on the less hindered reaction center.•TMSCl–TsONa is convenient reagent for silylation of organoaluminums.

Silyl esters of sulfonic acids are convenient and efficient silylating agents for β,β- and β-substituted 1-alkenylaluminums. The reaction proceeds at room temperature in CH2Cl2 or hexane for 18 h to give corresponding alkenylsilanes in high yield. At the same time, α,β-disubstituted and α,β,β-trisubstituted 1-alkenylaluminums were inert in the reaction under study. The reaction with aluminacyclopen-2-enes and aluminacyclopentanes takes place on the less sterically hindered reaction center. Using electron-donating solvents (diethyl ether, THF) inhibits the reaction. A new convenient procedure of silylation was developed, which consists in obtaining the silyl tosylate by the reaction of chlorosilanes with anhydrous sodium tosylate in toluene solution. The resulting reaction mixture was reacted with organoaluminum compounds without isolation of silyl tosylate.

Graphical abstractSilyl esters of sulfonic acids are efficient silylating agents for β,β- and β-substituted 1-alkenylaluminums. A new convenient procedure of silylation was developed, which consists in obtaining the silyl tosylate by the reaction of chlorosilanes with anhydrous sodium tosylate in toluene solution.Figure optionsDownload full-size imageDownload as PowerPoint slide