86767-25-1

Upstream product

• 122-00-9 para-methylacetophenone 
• 134-84-9 4-Methylbenzophenone 
• 74-88-4 methyl iodide 
• 333-27-7 methyl trifluoromethanesulfonate 
• 143-66-8 sodium tetraphenyl borate 
• 100-58-3 phenylmagnesium bromide 
• 676-58-4 methylmagnesium chloride 
• 106-38-7 para-bromotoluene 
• 98-86-2 acetophenone 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 90-90-4 (4-bromophenyl)(phenyl)methanone 
• 16635-23-7 phenyltriisopropoxytitanium(IV) 
• 917-54-4 methyllithium 
• 4294-57-9 para-methylphenylmagnesium bromide 

Downstream Products

• 41912-34-9 Phenyl-p'-methylphenylmethylcarbenium 
• 460742-62-5 4-nitro-benzoic acid 1-phenyl-1-p-tolyl-ethyl ester 
• 852822-59-4 tert-butyl 1-(4-methylphenyl)-1-phenylethyl peroxide 
• 98-86-2 acetophenone 
• 122-00-9 para-methylacetophenone 
• 948-55-0 1-phenyl-1-p-tolyl-ethylene 
• 110931-90-3 1-Phenyl-1-p-tolyl-aethyl-methylaether 
• 33863-82-0 4-methyl-N-(1-phenylethyl)aniline 
• 92645-93-7 N-phenyl-1-(4-methylphenyl)ethylamine 
• 1157634-93-9 1-phenyl-1-(p-tolyl)ethan-1-amine 
• 4209-16-9 N-phenyl-1-(p-tolyl)ethan-1-imine 
• 4209-15-8 N-(1-phenyl-ethylidene)-p-toluidine 
• 101292-15-3 1-Chlor-2-phenyl-2-p-tolyl-propan 
• 101594-47-2 p-<α,α-Dimethyl-benzyl>-phenyl-essigsaeure 

Relevant academic research and scientific papers

Hydroarylation of Alkenes by Protonation/Friedel-Crafts Trapping: HFIP-Mediated Access to Per-aryl Quaternary Stereocenters

Upon treatment with a combination of HFIP and an organic sulfonic acid, alkenes behave as Br?nsted bases and protonate to give carbocations which can be trapped by electron-rich arenes. The reaction constitutes a Friedel-Crafts hydroarylation which procee

Scandium(III) Trifluoromethanesulfonate Catalyzed Selective Reactions of Donor–Acceptor Cyclopropanes with 1,1-Diphenylethanols: An Approach to Polysubstituted Olefins

An unexpected synthetic approach to polysubstituted olefins through the scandium(III) trifluoromethanesulfonate catalyzed ring-opening reaction of donor–acceptor cyclopropanes with 1,1-diphenylethanols was developed. The reactions, which are experimentally easy to handle, feature tolerance of various functional groups and mild reaction conditions. On the basis of experimental evidence, a plausible mechanism was also proposed.

Catalytic Enantioselective Addition of Aryl Grignard Reagents to Ketones

We report a catalytic system for the challenging enantioselective addition of aryl Grignard reagents to ketones. Using a simple, one-pot procedure under mild conditions, a wide range of aromatic ketones are converted into diaryl alcohols in good yields and with good enantioselectivities. The catalytic enantioselective addition of aryl Grignard reagents to ketones is now possible. Using a readily available Ar-BINMOL ligand and titanium(IV) isopropoxide in a simple, one-pot procedure under mild conditions, a wide range of aromatic ketones are converted into diaryl alcohols in good yields and with good enantioselectivities.

Rhodium(I)-n-heterocyclic carbene-catalyzed addition of sodium tetraphenylborate to ketones to form tertiary alcohols

Rhodium complexes ([Rh(COD)(NHC)Cl]) were synthesized by the reaction of bis(1,3-dialkylperhydrobenzimidazolin-2-ylidene) with [RhClCOD]2 in toluene and characterized by elemental analysis, 1H NMR, 13C NMR and IR spectroscopy. These complexes were used as catalysts for the addition of sodium tetraphenylborate to aromatic ketones and corresponding tertiary alcohols were obtained in good yields.

Site-isolation and recycling of PdCl2 using PDMS thimbles

(Chemical Equation Presented) Macroscopic thimbles composed of polydimethylsiloxane (PDMS) were used to site-isolate PdCl2 from the products of Wacker-Tsuji oxidations and Pd-mediated homocouplings. The reactions were completed on the interior of hollow thimbles, and the organic products were isolated by their selective flux to the exterior of the thimbles. Although organic molecules had high flux through the walls of the thimbles, PdCl 2 remained encapsulated as a result of its polar structure that rendered it insoluble in PDMS. In two examples, less than 0.002% of the PdCl2 added to the interior of the thimble partitioned to the exterior; thus, over 99.998% remained encapsulated on the interior of the thimble. Because it was encapsulated, this catalyst was readily recycled five times for the Wacker-Tsuji oxidation of styrene. A sequential reaction was also completed where p-methylstyrene was oxidized to 4′-methyl-acetophenone by PdCl2 on the interior of a thimble and then fluxed to the exterior to react with phenylmagnesium bromide to yield 1-phenyl-1-p-tolyl-ethanol. This method site-isolated PdCl2 catalysts without requiring them to be rendered heterogeneous, the addition of exogenous ligands, or any modifications to the catalyst. The catalyst was site-isolated by affecting its environment rather than by altering its ligand structure.

APPARATUS AND METHOD FOR CARRYING OUT MULTIPLE REACTIONS

The invention provides methods and an apparatus useful for site-isolating reagents or catalysts during chemical reactions. The methods and apparatus are useful for carrying out cascade or domino reactions.

Rhodium-catalyzed addition of arylboron compounds to nitriles, ketones, and imines

The rhodium-catalyzed addition reactions of sodium tetraphenylborate and arylboronic acids to nitriles, ketones, and imines were examined. The reaction of nitriles could be carried out efficiently in the presence of a catalyst system of [RhCl(cod)]2-dppp and H2O to give the corresponding monoarylated products selectively. Although unactivated ketones and imines are known to be poor electrophiles for rhodium-catalyzed arylation, the phenylation of them with use of sodium tetraphenylborate proceeded smoothly in the presence of [RhCl(cod)]2 and Rh(acac)(cod) as catalysts, respectively. The addition of NH4Cl was found to be crucial to effectively conduct the reaction of ketones and imines.

Gold(I)-catalyzed oxidative cleavage of a C-C double bond in water

Oxidative cleavage of the C=C bond to afford ketone or aldehyde products with tert-butyl hydrogenperoxide (TBHP) as the oxidant can be catalyzed by AuCl with neocuproine (1) in water.

The effect of ring substitution on the O-neophyl rearrangement of 1,1-diarylalkoxyl radicals. A product and time-resolved kinetic study

A product and time-resolved kinetic study of the effect of ring substitution on the reactivity of 1,1-diarylalkoxyl radicals has been carried out. The radicals undergo an O-neophyl shift to give the isomeric 1-aryl-1-aryloxyalkyl radicals from which the corresponding aromatic ketones are formed. The rearrangement rate constants are influenced by ring substitution, increasing in the presence of electron-withdrawing substituents and decreasing in the presence of electron-donating ones. From the results of product and kinetic studies, the following migratory aptitudes have been obtained: 4-trifluoromethylphenyl > phenyl ? 4-methylphenyl > 4-methoxyphenyl. Excellent Hammett-type correlations between the σ+ substituent constants and both the visible absorption band maxima and the rearrangement rate constants have been obtained. The experimental results indicate that the rearrangement is governed by electronic effects in the starting 1,1-diarylalkoxyl radicals, whereas the stability of the rearranged carbon-centered radical plays a minor role, in line with a reactant-like transition state, strongly supporting the hypothesis that the O-neophyl rearrangement of 1,1-diarylalkoxyl radicals proceeds through a concerted mechanism.

Palladium-Catalyzed Methylation of Aryl and Vinyl Halides by Stabilized Methylaluminum and Methylgallium Complexes

The intramolecularly stabilized mono- and dialkylaluminum complexes 1a, 2, 3, 4a, 5a, 5c, 6a, 6c, 7, 8, and 9 in the presence of palladium catalysts, cross-alkylate aryl, vinyl, and benzyl bromides and iodides under mild standard laboratory conditions. Aryl bromides with carbonyl substituents or benzylic halides are converted partially into dialkyl compounds. Under similar conditions, the analogous stabilized dimethylgallium complexes 1b, 4b, 5b, 6b, and 10 methylate aryl and vinyl bromides and iodides in a highly selective manner. Substituted bromobenzenes XC6H4Br, where X = CHO, COPh, CO2Et, CN, NO2, Cl, CH2Br, or CH=CHCOPh, are methylated by the organogallium reagents usually only at the aromatic ring halogen atom to give substituted toluenes as single products. The methylation rates were shown to depend on the nature of the chelating ligands, on the solvent, and on the type of palladium catalyst employed.