Catalytic hydrosilylation of 1,3-diynes towards (E)-2-silylbut-1-en-3-ynes, (E,E)-2,3-disilylbuta-1,3-dienes and (E,E)-2-silyl1-3-silyl2buta-1,3-dienes

Abstract

Hydrosilylation of 1,3-diynes produced (E)-2-silylbut-1-en-3-ynes, (E,E)-2,3-disilylbuta-1,3-dienes, and (E,E)-2-silyl1-3-silyl2buta-1,3-dienes, which due to their complex structure and susceptibility to modification could be used in the preparation of drugs or natural compounds. The application of Pt2(dvs)3, PtO2, or [Ir(cod)Cl]2 (at room temperature or 40 ℃) allowed us to obtain (E)-2-silylbut-1-en-3-ynes. Their further modification in the presence of Pt2(dvs)3 or Pt(en)Cl2 (at 140 °C) led to the exclusive formation of (E,E)-2,3-disilylbuta-1,3-dienes, and (E,E)-2-silyl1-3-silyl2buta-1,3-dienes (a new family of compounds not yet obtained by other methods). For the first time, Pt(en)Cl2 was found to be effective in the hydrosilylation of 1,3-diynes, while [Ir(cod)Cl]2 compared to the literature, surprisingly gave (E)-2-silylbut-1-en-3-ynes instead of (E)-4-silylbut-1-en-3-ynes. Moreover, the first crystal structure of (E,E)-2,3-disilylbuta-1,3-diene was reported.