14311-00-3Relevant academic research and scientific papers
Palladium(0)-catalyzed silylation of aryl halides with triorganosilanes: Synthesis of aryl(2-furyl)silanes
Murata, Miki,Ohara, Hiroya,Oiwa, Ryo,Watanabe, Shinji,Masuda, Yuzuru
, p. 1771 - 1774 (2006)
Triorganosilanes, which possess two aryl groups on the silicon atom, undergo palladium-catalyzed silylation of aryl iodides. Aryl(2-furyl)silanes thus obtained are potentially useful starting materials for carbon-carbon bond-forming reactions in the prese
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.
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
supporting information, 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.).
Formal Nucleophilic Silyl Substitution of Aryl Halides with Silyllithium Reagents via Halogenophilic Attack of Silyl Nucleophiles
Yamamoto, Eiji,Ukigai, Satoshi,Ito, Hajime
, p. 2460 - 2464 (2017/10/06)
A new reaction has been developed for the formal nucleophilic silyl substitution of aryl halides with silyllithium or silylpotassium reagents. Dimethylphenylsilyllithium reacted with various aryl halides to form the corresponding arylsilanes in moderate to good yields with concomitant formation of the disilanes under the optimized reaction conditions. Mechanistic studies indicated that this silyl substitution reaction progresses through polar halogenophilic attack of silyl nucleophiles.
Palladium-catalyzed silylations of hydrosilanes with aryl halides using bulky alkyl phosphine
Yamanoi, Yoshinori
, p. 9607 - 9609 (2007/10/03)
A palladium-catalyzed direct trialkylsilyl transfer to aryl halides has been developed. In the presence of Pd(t-Bu3P)2 and K 3PO4, electron-rich para- or meta-substitute aryl iodides were coupled efficiently with triethylsilane, triphenylsilane, and dimethylphenylsilane to afford the corresponding silylated products in moderate to good yields.
