18402-55-6Relevant academic research and scientific papers
Silylation of Aryl Chlorides by Bimetallic Catalysis of Palladium and Gold on Alloy Nanoparticles
Miura, Hiroki,Masaki, Yosuke,Fukuta, Yohei,Shishido, Tetsuya
supporting information, p. 2642 - 2650 (2020/04/22)
Supported palladium-gold alloy-catalyzed cross-coupling of aryl chlorides and hydrosilanes enabled the selective formation of aryl-silicon bonds. Whereas a monometallic palladium catalyst predominantly promoted the hydrodechlorination of aryl chlorides and gold nanoparticles showed no catalytic activity, gold-rich palladium-gold alloy nanoparticles efficiently catalyzed the title reaction to give arylsilanes with high selectivity. A wide array of aryl chlorides and hydrosilanes participated in the heterogeneously-catalyzed reaction to furnish the corresponding arylsilanes in 34–80% yields. A detailed mechanistic investigation revealed that palladium and gold atoms on the surface of alloy nanoparticles independently functioned as active sites for the formation of aryl nucleophiles and silyl electrophiles, respectively, which indicates that palladium and gold atoms on alloy nanoparticles work together to enable the selective formation of aryl-silicon bonds. (Figure presented.).
Arylsilylation of aryl halides using the magnetically recyclable bimetallic Pd-Pt-Fe3O4 catalyst
Jang, Jisun,Byun, Sangmoon,Kim, B. Moon,Lee, Sunwoo
supporting information, p. 3492 - 3495 (2018/04/09)
Transition metal-catalyzed silylations have typically involved the use of homogeneous non-recyclable catalytic systems. In this work, the first example of a recyclable catalytic system for the synthesis of arylsilanes has been reported, which utilizes the
Decarbonylative Silylation of Esters by Combined Nickel and Copper Catalysis for the Synthesis of Arylsilanes and Heteroarylsilanes
Guo, Lin,Chatupheeraphat, Adisak,Rueping, Magnus
, p. 11810 - 11813 (2016/11/16)
An efficient nickel/copper-catalyzed decarbonylative silylation reaction of carboxylic acid esters with silylboranes is described. This reaction provides access to structurally diverse silanes with high efficiency and excellent functional-group tolerance
Diphenylphosphinite ionic liquid (IL-OPPh2): A solvent and ligand for palladium-catalyzed silylation and dehalogenation reaction of aryl halides with triethylsilane
Iranpoor, Nasser,Firouzabadi, Habib,Azadi, Roya
experimental part, p. 887 - 890 (2010/06/16)
The use of an imidazolium-based phosphinite ionic liquid (IL-OPPh2) as both solvent and ligand for Pd offers an efficient catalytic system for silylation of aryl iodides, bromides and also chlorides by triethylsilane in the presence of Cs2CO3. In the absence of base, this system is also performed for catalytic dehalogenation of aryl halides. The ionic liquid containing its corresponding Pd(0) complex can be easily recovered and reused in several runs without losing its efficiency.
Palladium-catalyzed silylation of electron-deficient aryl iodides using triorganosilane in the presence of pyridine and LiCl
Iizuka, Muneaki,Kondo, Yoshinori
supporting information; experimental part, p. 1161 - 1163 (2009/04/07)
Palladium-catalysed silylation of aryl iodides with electron-withdrawing groups was efficiently achieved using pyridine and lithium chloride as additives and conducting the reaction at room temperature. Functionalized aryl[2-(hydroxymethyl)-phenyl]dimethylsilanes were also prepared by palladium-catalysed reaction using THP-protected [2-(hydroxymethyl)-phenyl] dimethylsilane as a silylating agent followed by deprotection. Rhodium-catalysed 1,4-addition of the arylsilane was carried out using cyclohexenone as an enone in excellent yield. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Direct and selective arylation of tertiary silanes with rhodium catalyst
Yamanoi, Yoshinori,Nishihara, Hiroshi
, p. 6671 - 6678 (2008/12/22)
(Chemical Equation Presented) We have developed a convenient and efficient approach to the arylation of tertiary silanes under mild conditions. A variety of arylsilanes were synthesized in a one-step process with good to excellent yields in the presence of a rhodium catalyst with a base. The reaction was highly solvent dependent, and amides were the most effective of the various solvents used. This common catalyst system is highly tolerant of the various sensitive functional groups on the substrates, which might be difficult to extract by other methods. The rhodium-promoted silylation of aryl halides with electron-donating groups occurred more efficiently than the silylation of aryl halides substituted with electron-withdrawing groups. Heteroaromatic halides were also found to be readily silylated with tertiary silanes. The successful application of this reaction to the synthesis of a TAC-101 analogue, which is a trialkylsilyl-containing synthetic retinoid benzoic acid derivative with selective binding affinity for retinoic acid receptor-α, is also described.
