778-24-5Relevant academic research and scientific papers
Base-Mediated Borylsilylation/Silylation of Ammonium Salts with Silylborane
Du, Xian,Guan, Yun-Shi,Li, Yi-Hui,Liang, Guohai,Luo, Yong,Qi, Wan-Ying,Wang, Zi-Ying,Wei, Xun,Xu, Xiao-Hong,Yuan, Han,Zhen, Jing-Song
supporting information, p. 5988 - 5992 (2021/08/31)
This work describes a base-mediated borylsilylation of benzylic ammonium salts to synthesize geminal silylboronates bearing benzylic proton under mild reaction conditions. Deaminative silylation of aryl ammonium salts was also achieved in the presence of
A nickel-catalyzed silylation reaction of alkyl aryl sulfoxides with silylzinc reagents
Li, Wei-Ze,Wang, Zhong-Xia
supporting information, p. 5082 - 5086 (2021/06/21)
Ni(PEt3)Cl2-catalyzed silylation of alkyl aryl sulfoxides with silylzinc reagents was carried out. This protocol allows alkyl aryl sulfoxides to convert to arylsilicon compounds under mild reaction conditions, tolerates a range of functional groups and is suitable for a wide scope of substrates.
Continuous-flow Si-H functionalizations of hydrosilanesviasequential organolithium reactions catalyzed by potassiumtert-butoxide
Lee, Hyune-Jea,Kwak, Changmo,Kim, Dong-Pyo,Kim, Heejin
supporting information, p. 1193 - 1199 (2021/02/26)
We herein report an atom-economic flow approach to the selective and sequential mono-, di-, and tri-functionalizations of unactivated hydrosilanesviaserial organolithium reactions catalyzed by earth-abundant metal compounds. Based on the screening of various additives, we found that catalytic potassiumtert-butoxide (t-BuOK) facilitates the rapid reaction of organolithiums with hydrosilanes. Using a flow microreactor system, various organolithiums bearing functional groups were efficiently generatedin situunder mild conditions and consecutively reacted with hydrosilanes in the presence oft-BuOK within 1 min. We also successfully conducted the di-funtionalizations of dihydrosilane by sequential organolithium reactions, extending to a gram-scale-synthesis. Finally, the combinatorial functionalizations of trihydrosilane were achieved to give every conceivable combination of tetrasubstituted organosilane libraries based on a precise reaction control using an integrated one-flow system.
Hydrogenolysis of Polysilanes Catalyzed by Low-Valent Nickel Complexes
Comas-Vives, Aleix,Eiler, Frederik,Grützmacher, Hansj?rg,Pribanic, Bruno,Trincado, Monica,Vogt, Matthias
supporting information, p. 15603 - 15609 (2020/04/29)
The dehydrogenation of organosilanes (RxSiH4?x) under the formation of Si?Si bonds is an intensively investigated process leading to oligo- or polysilanes. The reverse reaction is little studied. To date, the hydrogenolysis of Si?Si bonds requires very harsh conditions and is very unselective, leading to multiple side products. Herein, we describe a new catalytic hydrogenation of oligo- and polysilanes that is highly selective and proceeds under mild conditions. New low-valent nickel hydride complexes are used as catalysts and secondary silanes, RR′SiH2, are obtained as products in high purity.
METHOD FOR PRODUCING ARYLSILANE COMPOUND CONTAINING HALOSILANE COMPOUND AS RAW MATERIAL
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Paragraph 0087-0091, (2020/03/06)
PROBLEM TO BE SOLVED: To provide a method for producing an arylsilane compound with low production cost. SOLUTION: A method for producing an arylsilane compound includes a reaction step for the cross-coupling reaction of a halosilane compound represented by general formula (A-1), (A-2), or (A-3) and an arylboronic acid pinacol ester in the presence of a nickel catalyst, a Lewis acid catalyst, and an organic base (R independently represent an aromatic hydrocarbon group, a heteroaromatic ring group, or a C1-20 hydrocarbon group; X independently represent a halogeno group or a trifluoromethanesulfonyloxy group). SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
Nickel-Catalyzed Decarbonylation of Acylsilanes
Ito, Yuri,Kodama, Takuya,Nakatani, Syun,Sakurai, Shun,Tobisu, Mamoru
, p. 7588 - 7594 (2020/06/27)
Nickel-catalyzed decarbonylation of acylsilanes is developed. In sharp contrast to cross-coupling reactions of acylsilanes, in which the silyl group serves as a leaving group, the silyl group is retained in the product in this decarbonylation reaction. Although the strong binding of the dissociated CO to the nickel center frequently hinders catalyst turnover in nickel-mediated decarbonylative reactions, this reaction can be catalyzed by nickel complexes bearing a CO ligand.
Dimethylformamide-stabilised palladium nanoclusters catalysed coupling reactions of aryl halides with hydrosilanes/disilanes
Nagata, Tatsuki,Inoue, Takeru,Lin, Xianjin,Ishimoto, Shinya,Nakamichi, Seiya,Oka, Hideo,Kondo, Ryota,Suzuki, Takeyuki,Obora, Yasushi
, p. 17425 - 17431 (2019/06/24)
N,N-Dimethylformamide-stabilised Pd nanocluster (NC) catalysed cross-coupling reactions of hydrosilane/disilane have been investigated. In this reaction, the coupling reaction proceeds without ligands with low catalyst loading. N,N-Dimethylacetamide is a crucial solvent in these reactions. The solvent effect was considered by various techniques, such as transmission electron microscopy, X-ray photoelectron spectroscopy, and thermogravimetric analysis. The Pd NCs can be recycled five times under both hydrosilane and disilane reaction conditions.
Nickel-Catalyzed Reaction of Aryl 2-Pyridyl Ethers with Silylzinc Chlorides: Silylation of Aryl 2-Pyridyl Ethers via Cleavage of the Carbon?Oxygen Bond
Kong, Ying-Ying,Wang, Zhong-Xia
, p. 5440 - 5448 (2019/11/16)
Ni-catalyzed C?O(Py) bond activation and silylation of aryl 2-pyridyl ethers with silylzinc chlorides were carried out. This protocol allowed the 2-pyridyloxy group to be substituted by a silyl group with short reaction times, mild reaction conditions, and good compatibility of functional groups. (Figure presented.).
Nickel-Catalyzed Synthesis of Silanes from Silyl Ketones
Srimontree, Watchara,Lakornwong, Waranya,Rueping, Magnus
supporting information, p. 9330 - 9333 (2019/11/19)
An unprecedented nickel-catalyzed decarbonylative silylation via CO extrusion intramolecular recombination fragment coupling of unstrained and nondirecting group-Assisted silyl ketones is described. The inexpensive and readily available catalyst performs
In Situ Generation of Silyl Anion Species through Si?B Bond Activation for the Concerted Nucleophilic Aromatic Substitution of Fluoroarenes
Kojima, Kumiko,Nagashima, Yuki,Wang, Chao,Uchiyama, Masanobu
, p. 277 - 280 (2019/04/04)
In situ generated silyl anion species enable the concerted nucleophilic aromatic substitution of fluoroarenes. Model DFT calculations indicated that addition of a base to a silylborane would thermodynamically form a silyl borate complex and then kinetically release a silyl anion species through Si?B bond cleavage, and that the in situ generated silyl anion equivalent would further react with a fluoroarene through a concerted nucleophilic aromatic substitution pathway with an activation barrier of ca. 20 kcal/mol to afford the silylated product with a large energy gain. Experiments confirmed that the defluorosilylation reaction took place smoothly at room temperature simply upon mixing fluoroarenes with commercially available silylborane and NaOtBu. Radical scavenger and radical clock reaction experiments provide further evidence for the in situ generation of the silyl anion.
