7450-03-5

Upstream product

• 932-31-0 ortho-tolylmagnesium bromide 
• 75-77-4 chloro-trimethyl-silane 
• 6699-93-0 (2-methylphenyl)lithium 
• 5796-98-5 bis-trimethylsilanyl peroxide 
• 95-49-8 2-methylchlorobenzene 
• 95-46-5 2-methylphenyl bromide 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 108-88-3 toluene 
• 10090-05-8 trimethylsilyl methanesulfonate 
• 529-19-1 2-Methylbenzonitrile 
• 42908-77-0 1-methyl-2-(trifluoromethoxy)benzene 
• 95-52-3 2-Fluorotoluene 
• 109-72-8 n-butyllithium 
• 56174-66-4 2-(N,N-dimethylaminomethyl)phenyllithium 

Downstream Products

• 527-84-4 2-methylisopropylbenzene 
• 535-77-3 m-cymene 
• 99-87-6 4-methylisopropylbenzene 
• 108-88-3 toluene 
• 577-16-2 2-Methylacetophenone 
• 16216-13-0 2-phenyl-1-o-tolylethanone 
• 32641-95-5 Benzyl 4-methyl-3-(trimethylsilyl)phenylketon 
• 32641-97-7 2-Methyl-3'-nitro-benzophenon 
• 3728-43-6 p-(trimethylsilyl)toluene 
• 3728-44-7 3-(trimethylsilyl)toluene 
• 73177-92-1 (2-methylphenyl)(phenyl)iodonium tosylate 
• 156629-31-1 dibromo(o-tolyl)borane 
• 1252609-65-6 C₂₁H₂₃NO₃ 
• 88986-00-9 9-(o-tolyl)phenanthrene 

Relevant academic research and scientific papers

Cobalt-Catalyzed Defluorosilylation of Aryl Fluorides via Grignard Reagent Formation

Transition-metal-catalyzed transformations of the carbon-fluorine bond not only tackle an interesting problem of challenging bond activation but also offer new synthetic strategies where the relatively inert C-F bond is converted to versatile functional groups. Herein we report a practical cobalt-catalyzed silylation of aryl fluorides that uses a cheap electrophilic silicon source with magnesium. This method is compatible with various silicon sources and can be operated under aerobic conditions. Mechanistic studies support the in situ formation of a Grignard reagent, which is captured by the electrophilic silicon source.

Oxidative 1,2-Difunctionalization of Ethylene via Gold-Catalyzed Oxyarylation

Under the conditions of oxidative gold catalysis, exposure of ethylene to aryl silanes and alcohols generates products of 1,2-oxyarylation. This provides a rare example of a process that allows catalytic differential 1,2-difunctionalization of this feedstock chemical.

Cationic Chiral Fluorinated Oxazaborolidines. More Potent, Second-Generation Catalysts for Highly Enantioselective Cycloaddition Reactions

The coordination of chiral ligands to Lewis acid metal derivatives, a useful strategy for enantioselective, electrophilic catalysis, generally leads to a lower level of catalytic activity than that of the original uncomplexed compound. Activation by furth

Gold-catalysed oxyarylation of styrenes and mono- and gem-disubstituted olefins facilitated by an iodine(III) oxidant

1-Hydroxy-1,2-benziodoxol-3(1H)-one (IBA) is an efficient terminal oxidant for gold-catalysed, three-component oxyarylation reactions. The use of this iodine(III) reagent expands the scope of oxyarylation to include styrenes and gem-disubstituted olefins, substrates that are incompatible with the previously reported Selectfluor-based methodology. Diverse arylsilane coupling partners can be employed, and in benzotrifluoride, homocoupling is substantially reduced. In addition, the IBA-derived co-products can be recovered and recycled. The I's have it: The unprecedented use of an iodine(III) reagent as the terminal oxidant for gold-catalysed oxyarylation allows the substrate scope to be significantly expanded; in addition to monosubstituted olefins, styrenes and gem-disubstituted olefins are well tolerated (see scheme). With benzotrifluoride as solvent, unproductive homodimerisation of the arylsilane coupling partner is effectively suppressed. Copyright

Palladium-catalyzed direct CH bond arylation of simple arenes with aryltrimethylsilanes

Direct CH bond arylation of arenes with aryltrimethylsilanes catalyzed by PdCl2 in the presence of CuCl2 as an oxidant has been developed. In addition to the role as the oxidant, CuCl2 is found to be necessary for the selective crosscoupling reaction.

Arylsilanes: Application to gold-catalyzed oxyarylation of alkenes

Arylsilanes are efficient reagents for the gold-catalyzed oxyarylation of alkenes (21 examples, up to 85% isolated yield). Using commercially available Ph3PAuCl and readily prepared, benign arylsilanes, these two- and three-component reactions

Highly Enantioselective diels-alder reactions of maleimides catalyzed by activated chiral oxazaborolidines

[Chemical equation presented] Diels-Alder reactions of various combinations of maleimides and 1,3-dienes with cationic oxazaborolidines as catalysts have been shown to be highly efficient and enantioselective.

Selective aromatic carbon-oxygen bond cleavage of trifluoromethoxyarenes: a trifluoromethoxy group as a convertible directing group

An efficient method for selective activation of aromatic C-O bonds in trifluoromethoxyarenes is developed. Upon treatment with a metallic sodium/chlorotrimethylsilane system, trifluoromethoxyarenes undergo reductive dealkoxylation to provide the corresponding arylsilanes. Also the synthetic applications of the present reactions combined with ortho-metallation are described.

Method of producing an o-disubstituted aromatic compound, and method of producing a monosubstituted-monohaloaromatic compound

A method of producing an o-disubstituted aromatic compound, containing: continuously conducting at least the following steps (a) to (d): (a) a step of mono-lithiating one halogen atom of an o-dihaloaromatic compound, using a first microreactor; (b) a step of making the thus-obtained monolithiated product to react with an electrophilic compound, using a second microreactor, to obtain a monosubstituted-monohaloaromatic compound; (c) a step of lithiating the other halogen atom of the o-dihaloaromatic compound, using a third microreactor; and (d) a step of making the thus-obtained lithiated product successively to react with an electrophilic compound, using a forth microreactor.

Rhodium-catalyzed silylation and intramolecular arylation of nitriles via the silicon-assisted cleavage of carbon-cyano bonds

A rhodium-catalyzed silylation reaction of carbon - cyano bonds using disilane has been developed. Under these catalytic conditions, carbon-cyano bonds in aryl, alkenyl, allyl, and benzyl cyanides bearing a variety of functional groups can be silylated. The observation of an enamine side product in the silylation of benzyl cyanides and related stoichiometric studies indicate that the carbon-cyano bond cleavage proceeds through the deinsertion of silyl isocyanide from η2-iminoacyl complex B. Knowledge gained from these studies has led to the development of a new intramolecular biaryl coupling reaction in which aryl cyanides and aryl chlorides are cross-coupled.