Ruthenium-catalysed hydrosilylation of carbon–carbon multiple bonds

Abstract

Recent advances in ruthenium-catalysed hydrosilylation of C–C multiple bonds and its application to organic synthesis are highlighted.

Iridium-catalyzed Markovnikov hydrosilylation of terminal alkynes achieved by using a trimethylsilyl-protected trihydroxysilane

“…2). Both of propargyl alcohol and a variety of its derivatives were highly regioselectively hydrosilylated under this catalytic system, affording related products in good to excellent yields (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11). Hydrosilylation of electron-deficient propargylic acid and methyl propiolate proceeded with high efficiency and regioselectivity (12 and 13).…”

“…1 H and 13 C NMR Spectra of all hydrosilylation products and unknown substrate were provided. 13 C DEPT135 NMR Spectra of products 3,4,5,6,7,9,10,12,13,15,19,20,21,26,30,31,32,36,37,38,39,40,41,42,44,45 were afford. 2D NOESY Results of products 1 and 27 are also provided.…”

“…In recent years, this problem has been partially addressed with the developments of several efficient protocols . For instance, Ru-based complexes have been developed as the predominant catalysts for this field since the pioneering works from Trost and Yamamoto, et al [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] . Co-catalyzed α-hydrosilylation of alkynes showed superiority in modification of aryl alkynes [19][20][21][22][23] .…”

Catalytic Formation of Silicon–Heteroatom (N, P, O, S) Bonds

“…Among the approaches, hydrosilylation seems to be an extremely attractive route given the fact that this reaction is compatible with the atom‐economy strategy. The catalytic addition of Si−H to unsaturated substrates has emerged in recent decades (Scheme ) . It allows a wide range of important organosilicon molecules that are used in the agrochemical, pharmaceutical, and fine‐chemical industries to be obtained .…”

Regioselective formation of β‐(E)‐ and α‐alkenylsilane moiety attached to silsesquioxane core via Pt‐ and Ru‐based hydrosilylation

“…The reaction proceeds in the presence of many types of homogeneous late TM catalysts, e.g. platinum, ruthenium, rhodium and iridium, as well as early TM complexes such as those of titanium or lanthanides, but also heterogeneous systems, or even Lewis acids . In the case of terminal alkynes, controlling the stereo‐ or regioselectivity of the process is crucial because this reaction can afford multiple products, including α‐, β‐( E )‐ and β‐( Z )‐vinylsilanes.…”