92722-80-0Relevant academic research and scientific papers
Highly selective electroreductive linear dimerization of electron-deficient vinylarenes
Ning, Shulin,Zheng, Lianyou,Bai, Ya,Wang, Shutao,Wang, Siyu,Shi, Lingling,Gao, Qiansong,Che, Xin,Zhang, Zhuoqi,Xiang, Jinbao
supporting information, (2021/11/16)
A direct electroreductive dimerization of electron-deficient vinylarenes for the synthesis of 1,4-diarylbutane has been developed using a simple undivided cell with inexpensive carbon electrodes at room temperature. The control and deuterium-labeling experiments of electroreductive dimerization suggest that the hydrogen source comes from the solvent CH3CN. This protocol provides a mild and efficient route for the construction of C–C bond in moderate to good yields with high regioselectivity and broad substrate scope.
Silicon-Based Cross-Coupling Reagent and Production Method of Organic Compound Using the Same
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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.
Improved Julia-Kocienski conditions for the methylenation of aldehydes and ketones
Aissa, Christophe
, p. 360 - 363 (2007/10/03)
The scope of the methylenation of aldehydes and ketones under optimized Julia-Kocienski conditions is broadened by using 1-tert-butyl-1H-tetrazol-5- ylmethyl sulfone. Two different Barbier-type procedures are applied with NaHMDS at -78 °C or Cs2CO3 at 70 °C. The latter conditions are also adapted for the preparation of 1,2-disubstituted olefins and intramolecular olefination 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
