Direct Process for Preparation of Arylhalosilanes

Barry, A. J.; Gilkey, John W.; Hook, D. E.

doi:10.1021/ba-1959-0023.ch023

Cited by 8 publications

(3 citation statements)

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“…The synthesis of arylsilanesimportant intermediates in the silicone industryis an excellent case in point. The common methods such as the Direct (Rochow) Process and the Barry Process cannot be adapted for most specialty arylsilanes and mixed aryl−alkyl silanes, which must be produced using Grignard or lithium reagents. As a result, one focus of our research efforts has been the discovery of new catalytic methods for the formation of silicon−carbon bonds, especially arylsilanes.…”

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confidence: 99%

Catalytic C−H Bond Functionalization: Synthesis of Arylsilanes by Dehydrogenative Transfer Coupling of Arenes and Triethylsilane

et al. 1998

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A new catalytic route for the formation of arene−silicon bonds based on the transfer dehydrogenative coupling of triethylsilane with an arene (Ar−X: X = −CF3, −F, −H, −CH3, −Cl, −Br) in the presence of 3,3-dimethylbut-1-ene (tBu-ethylene) is reported. Rhodium and ruthenium catalysts (η5-C5Me5)Rh(H)2(SiEt3)2 and (η6-arene)Ru(H)2(SiEt3)2 and their corresponding dimeric chloride precursors not only catalyze the coupling of Et3SiH with an arene but additionally promote the dimerization of Et3SiH producing a carbosilane, Et3Si−CHMe−SiEt2H.

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confidence: 99%

Catalytic C−H Bond Functionalization: Synthesis of Arylsilanes by Dehydrogenative Transfer Coupling of Arenes and Triethylsilane

et al. 1998

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“…In the late 1950s, Dow chemists developed a methodology for C−H silylation of benzene using borontrichloride as a catalyst with trichlorosilane ( 97 , 40% yield, Scheme 22). [35–37,3b] …”

Section: Lewis Acid Catalyzed C−h Silylationmentioning

confidence: 99%

Transition‐Metal‐Free C−H Silylation: An Emerging Strategy

et al. 2021

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Silicon‐containing molecules are of great interest with widespread applications in several research areas such as polymer chemistry, materials science, medicinal chemistry, and complex molecule synthesis. Transition‐metal‐free C−H silylation is an essential process because this process is useful in fabricating carbon‐silicon bonds which can be further transformed into a number of other compounds. Since transition‐metal‐catalyzed C−H bond silylation is a developed field, therefore this context only contains transition‐metal‐free pathways for transforming C−H bond to C−Si (Si=SiR3) bond. This review has been further categorized and subcategorized based on intermediates involved and catalysts used during this transformation. This synopsis summarizes recent developments in the area of silicon chemistry with a focus of innovative transition‐metal‐free catalytic silylation using different strategies such as free radical, base promoted, Brønsted acid, Lewis acid, and frustrated Lewis pair.

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“…Driven by the versatility of (hetero)aryl silanes as synthons in organic synthesis and their interest in medicinal and materials science, the recent years have witnessed the design of metal-catalyzed sp 2 C–H silylation reactions . While the coupling of electron-rich or electron-neutral (hetero)arenes has become routine, , sp 2 C–H silylation strategies of electron-deficient azines remain currently confined to C3-selective processes with noble Ir or Ru catalysts (Scheme , path b ) . Therefore, at the outset of our investigations it was unclear whether a switchable C2/C4–H silylation of pyridines could be developed without steric and electronic bias .…”

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confidence: 99%