853955-58-5Relevant academic research and scientific papers
Straightforward synthesis of HOMSi reagents via sp2 C-H silylation
Minami, Yasunori,Komiyama, Takeshi,Hiyama, Tamejiro
supporting information, p. 1053 - 1055 (2015/09/02)
Straightforward C-H silylation of heteroarenes and alkenes was found to provide efficient access to organo-HOMSi reagents as stable silicon reagents for cross-coupling. Various heteroarenes and terminal alkenes were silylated to show the versatility of the reaction. This method was applied in double silylation reactions to give bisHOMSi reagents. The silylation products could be used in the cross-coupling reaction with haloarenes easily.
Copper-catalyzed electrophilic amination of arylsilanes with hydroxylamines
Miki, Yuya,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
supporting information, p. 172 - 175 (2013/03/28)
A copper-catalyzed electrophilic amination of aryl[(2-hydroxymethyl)phenyl] dimethylsilanes with O-acylated hydroxylamines has been developed to afford the corresponding anilines in good yields. The catalytic reaction proceeds very smoothly under mild conditions and tolerates a wide range of functional groups.
Improved Hiyama cross-coupling reactions using HOMSi
Marcuccio, Sebastian M.,Epa, Ruwan,Moslmani, Maisa,Hughes, Andrew B.
scheme or table, p. 7178 - 7181 (2012/01/14)
Various parameters in the Hiyama cross-coupling reaction of HOMSi reagents with ethyl bromobenzoate were studied. These included solvent, ligand, palladium source, and added water. DMF and THF were found to be excellent solvents. Palladium chloride was found to be the best palladium source and no added water was required. The use of tri-o-tolylphosphine as the ligand proved to be particularly effective.
Silicon-Based Cross-Coupling Reagent and Production Method of Organic Compound Using the Same
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Page/Page column 12-13, (2009/04/24)
In one embodiment of the present invention, a silicon-based cross-coupling reagent is disclosed which is a highly stable tetraorganosilicon compound allowing for a cross-coupling reaction under mild reaction conditions without using fluoride ions, transition metal promoter, or strong bases, and the residue of the silicon reagent can be recovered and reused. The silicon-based cross-coupling reagent is a silicon compound in which an o-hydroxymethylphenyl group is connected to a silicon atom for intramolecular activation.
Synthesis and cross-coupling reaction of alkenyl[(2-hydroxymethyl)phenyl]dimethylsilanes
Nakao, Yoshiaki,Imanaka, Hidekazu,Chen, Jinshui,Yada, Akira,Hiyama, Tamejiro
, p. 585 - 603 (2008/02/06)
Highly stable alkenyl[2-(hydroxymethyl)phenyl]dimethylsilanes are prepared by stereo- and regioselective hydrosilylation of alkynes catalyzed either by a platinum or ruthenium catalyst using protected [2-(hydroxymethyl)phenyl]dimethylsilanes. Cyclic silyl ether, 1,1-dimethyl-2-oxa-1-silaindan, also serves as a starting material for the alkenylsilanes by the ring-opening reaction with alkenyl Grignard reagents. The resulting alkenylsilanes undergo cross-coupling reaction with various aryl and alkenyl iodides under reaction conditions employing K2CO3 as a base at 35-50 °C in highly regio- and stereospecific manners. The reaction tolerates a diverse range of functional groups including silyl protections. The silicon residue is readily recovered and reused on a gram-scale synthesis. Intramolecular coordination of a proximal hydroxyl group is considered to efficiently form pentacoordinate silicates having a transferable group possibly at an axial position and, thus, responsible for the cross-coupling reaction under conditions significantly milder than those reported for the silicon-based reactions.
Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes: An entry to tetraorganosilicon reagents for the silicon-based cross-coupling reaction
Nakao, Yoshiaki,Imanaka, Hidekazu,Sahoo, Akhila K.,Yada, Akira,Hiyama, Tamejiro
, p. 6952 - 6953 (2007/10/03)
Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes, highly stable tetraorganosilicon reagents, are found to react with aryl and alkenyl iodides in the presence of a palladium catalyst and K2CO3 as a base, significantly milder conditions compared with those ever reported for the silicon-based cross-coupling reactions. The reaction tolerates a wide range of functional groups, including silyl protectors, and allows a gram-scale synthesis to recover and reuse the silicon residue. Copyright
