A new protocol for synthesis of bifunctional alkynyl[vinyl or (E)-alkenyl]substituted organosilicon compounds

A new efficient route for selective synthesis of various, novel alkynyl(vinyl)substituted silicon (6) and alkynyl[(E)-alkenyl]substituted silicon compounds (9) via silylative coupling of alkynes and their products catalyzed by ruthenium(+2) complexes is described. The tandem procedure facilitates the formation of 9 synthesized in a high yield and stereoselectivity by a sequential silylative coupling of terminal alkynes with divinylsubstituted silicon compounds followed by silylative coupling reaction of 6 with styrenes in the presence of ruthenium hydride complexes ([RuHCl(CO)(PR3)3−n]; R = Cy (n = 1), i-Pr (n = 1), Ph (n = 0)).

Graphical abstractA new efficient route for selective synthesis of various, novel alkynyl(vinyl)substituted silicon (6) and alkynyl[(E)-alkenyl]substituted silicon compounds (9) via silylative coupling of alkynes and their products catalyzed by ruthenium(+2) complexes is described. The tandem procedure facilitates the formation of 9 synthesized in a high yield and stereoselectivity by a sequential silylative coupling of terminal alkynes with divinylsubstituted silicon compounds followed by silylative coupling reaction of 6 with styrenes in the presence of ruthenium hydride complexes ([RuHCl(CO)(PR3)3−n]; R = Cy (n = 1), i-Pr (n = 1), Ph (n = 0)).Figure optionsDownload full-size imageDownload as PowerPoint slideResearch highlights► Alkynyl[vinyl or (E)-alkenyl]substituted organosilicon compounds are attractive starting materials for organometallic synthesis. ► Alkynyl or styryl functionality can be efficiently introduced to divinylsubstituted organosilicon compounds. ► Silylative coupling and its tandem procedure facilitates the formation of such type of compounds.