129182-22-5Relevant academic research and scientific papers
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 (2005)
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
Palladium-catalyzed heck reaction of aryl chlorides under mild conditions promoted by organic ionic bases
Xu, Hua-Jian,Zhao, Yong-Qiang,Zhou, Xin-Feng
experimental part, p. 8036 - 8041 (2011/12/02)
An efficient Pd-catalyzed Heck reaction of aryl chlorides with olefins under mild conditions is described. High yields of products were achieved with n-Bu4N+OAc- as base. Significantly, the temperature of the Heck reaction of diverse nonactivated aryl chlorides can be lowered to 80 °C. The new reaction system can also tolerate a wider range of olefins.
Silicon-Based Cross-Coupling Reagent and Production Method of Organic Compound Using the Same
-
Page/Page column 16, (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.
Palladium-tetraphosphine catalysed heck reaction with simple alkenes: Influence of reaction conditions on the migration of the double bond
Fall, Yacoub,Berthiol, Florian,Doucet, Henri,Santelli, Maurice
, p. 1683 - 1696 (2008/02/08)
The Heck reaction of aryl halides with simple alk-1-enes is a powerful method for the synthesis of (E)-1-arylalk-1-ene derivatives. The major problem of this reaction is the palladium-catalysed migration of the carbon-carbon double bond along the alkyl ch
A wide range of organosilicon compounds couples with enol and aryl triflates in the presence of Pd catalyst and fluoride ion
Hatanaka, Yasuo,Hiyama, Tamejiro
, p. 2719 - 2722 (2007/10/02)
Under the influence of tetrakis(triphenylphosphine)palladium and tetrabutylammonium fluoride, the title reaction took place with alkenyl, alkynyl, aryl, and alkylsilanes to give the corresponding coupled products in good yields with high chemoselectivity and stereospecificity.
