3575-19-7

Upstream product

• 98-82-8 Isopropylbenzene 
• 826-55-1 2-methyl-2-phenylpropionic acid 
• 79373-26-5 2-Phenyl-2-(tetrahydropyran-2-yloxy)propane 
• 617-94-7 1-methyl-1-phenylethyl alcohol 
• 98-83-9 isopropenylbenzene 

Downstream Products

• 935-67-1 Cumyl methyl ether 
• 19219-89-7 2-Methyl-2-phenylhexane 
• 1712-74-9 ethyl cumyl ether 
• 4406-52-4 (1,1,3-trimethylbutyl)benzene 
• 26356-11-6 2,3-dimethyl-2-phenylbutane 
• 1889-67-4 dicumene 
• 37872-12-1 1,1,2,2-tetramethyl-1-phenylpropane 
• 22115-03-3 (1,1,4-trimethyl-pentyl)-benzene 
• 93449-07-1 1-(α-bromo-isopropyl)-4-chloro-benzene 
• 70887-31-9 3-(1-Methyl-1-phenylethyl)pentan-2,4-dion 
• 98821-10-4 2-(Methylthio)-2-phenylpropane 
• 125847-17-8 2-methyl-1-(4-methylphenyl)-1,2-diphenylpropane 
• 40673-57-2 1,1,2,2-tetra(p-tolyl)ethane 
• 125847-18-9 2-methyl-1,1-bis(4-methylphenyl)-2-phenylpropane 

Relevant academic research and scientific papers

Methane Generation and Reductive Debromination of Benzylic Position by Reconstituted Myoglobin Containing Nickel Tetradehydrocorrin as a Model of Methyl-coenzyme M Reductase

Methyl-coenzyme M reductase (MCR), which contains the nickel hydrocorphinoid cofactor F430, is responsible for biological methane generation under anaerobic conditions via a reaction mechanism which has not been completely elucidated. In this work, myoglobin reconstituted with an artificial cofactor, nickel(I) tetradehydrocorrin (NiI(TDHC)), is used as a protein-based functional model for MCR. The reconstituted protein, rMb(NiI(TDHC)), is found to react with methyl donors such as methyl p-toluenesulfonate and trimethylsulfonium iodide with methane evolution observed in aqueous media containing dithionite. Moreover, rMb(NiI(TDHC)) is found to convert benzyl bromide derivatives to reductively debrominated products without homocoupling products. The reactivity increases in the order of primary > secondary > tertiary benzylic carbons, indicating steric effects on the reaction of the nickel center with the benzylic carbon in the initial step. In addition, Hammett plots using a series of para-substituted benzyl bromides exhibit enhancement of the reactivity with introduction of electron-withdrawing substituents, as shown by the positive slope against polar substituent constants. These results suggest a nucleophilic SN2-type reaction of the Ni(I) species with the benzylic carbon to provide an organonickel species as an intermediate. The reaction in D2O buffer at pD 7.0 causes a complete isotope shift of the product by +1 mass unit, supporting our proposal that protonation of the organonickel intermediate occurs during product formation. Although the turnover numbers are limited due to inactivation of the cofactor by side reactions, the present findings will contribute to elucidating the reaction mechanism of MCR-catalyzed methane generation from activated methyl sources and dehalogenation.

Thiourea-Mediated Halogenation of Alcohols

The halogenation of alcohols under mild conditions expedited by the presence of substoichiometric amounts of thiourea additives is presented. The amount of thiourea added dictates the pathway of the reaction, which may diverge from the desired halogenation reaction toward oxidation of the alcohol, in the absence of thiourea, or toward starting material recovery when excess thiourea is used. Both bromination and chlorination were highly efficient for primary, secondary, tertiary, and benzyl alcohols and tolerate a broad range of functional groups. Detailed electron paramagnetic resonance (EPR) studies, isotopic labeling, and other control experiments suggest a radical-based mechanism. The fact that the reaction is carried out at ambient conditions, uses ubiquitous and inexpensive reagents, boasts a wide scope, and can be made highly atom economic, makes this new methodology a very appealing option for this archetypical organic reaction.

In Situ Generated Gold Nanoparticles on Active Carbon as Reusable Highly Efficient Catalysts for a Csp3 ?Csp3 Stille Coupling

Gold nanoparticle catalysts are important in many industrial production processes. Nevertheless, for traditional Csp2-Csp2 cross-coupling reactions they have been rarely used and Pd catalysts usually give a superior performance. Herein we report that in situ formed gold metal nanoparticles are highly active catalysts for the cross coupling of allylstannanes and activated alkylbromides to form Csp3-Csp3 bonds. Turnover numbers up to 29 000 could be achieved in the presence of active carbon as solid support, which allowed for convenient catalyst recovery and reuse. The present study is a rare case where a gold metal catalyst is superior to Pd catalysts in a cross-coupling reaction of an organic halide and an organometallic reagent.

HBr–DMPU: The First Aprotic Organic Solution of Hydrogen Bromide

HBr and DMPU (1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone) form a room-temperature-stable complex that provides a mild, effective, and selective hydrobrominating reagent toward alkynes, alkenes, and allenes. HBr–DMPU could also replace other halogenating reagents in the halo-Prins reaction, ether cleavage, and deoxy-bromination reactions.

Direct halogenation of alcohols with halosilanes under catalyst- and organic solvent-free reaction conditions

A chemoselective method for the direct halogenation of different types of alcohols with halosilanes under catalyst- and solvent-free reaction conditions (SFRC) is reported. Various primary, secondary and tertiary benzyl alcohols and tertiary alkyl alcohols were directly transformed to the corresponding benzyl and alkyl halides, respectively, using chlorotrimethylsilane (TMSCl) and bromotrimethylsilane (TMSBr).

Iron-catalyzed borylation of alkyl electrophiles

The use of low-cost iron(III) acetoacetate (Fe(acac)3) and tetramethylethylenediamine (TMEDA) enables the direct cross-coupling of alkyl halides with bis(pinacolato)diboron. This approach allows for the borylation of activated or unactivated primary, secondary, and tertiary bromides. Moreover, even the borylation of benzylic or allylic chlorides, tosylates, and mesylates are possible. The reactions proceed under mild conditions at room temperature and show broad functional-group compatibility and "robustness" as measured by a modified Glorius robustness screen.

Bromination of alkylbenzenes in 1-butyl-3-methylimidazolium bromide and its dibromide complex

Alkylbenzenes were subjected to bromination with molecular bromine using 1-butyl-3-methylimidazolium bromide as solvent. A complex of 1-butyl-3-methylimidazolium bromide with bromine was synthesized. It ensured bromination of alkylbenzenes with no bromine and solvent. The results of bromination in binary solvents and ionic liquids, 1-butyl-3-methylimidazolium bromide and tribromide were compared. The bromination of ethylbenzene with 1-butyl-3-methylimidazolium tribromide was accompanied by formation of a considerable amount of α-bromoethylbenzene, which is not typical of electrophilic aromatic substitution process.

Hexabromoacetone and ethyl tribromoacetate: a highly efficient reagent for bromination of alcohol

A new and efficient method for the bromination of alcohols utilizing Br3CCOCBr3/PPh3 and Br3CCO2Et/PPh3 is described. Various alcohols can be converted smoothly into their corresponding alkyl bromides in high yields under mild conditions with short reaction times. Based upon 1H NMR studies using competitive reactions between selected brominating agents and Cl3CCN, Br3CCOCBr3 displays the highest reactivity approximately nine times that of CBr4.

Palladium-catalyzed intramolecular arylation of N-benzyl-2-iodoimidazoles: A facile and rapid access to 5H-imidazo[2,1-α]isoindoles

The first example of a Pd-catalyzed intramolecular arylation involving the C-2 position of an imidazole ring is presented. Application of this reaction led to the formation of 5H-imidazo[2,1-a]isoindole in one step from N-benzyl-2-iodoimidazole. Microwave irradiation enhanced the rate of reaction allowing the synthesis of various imidazo[2,1-a]isoindole analogues. Georg Thieme Verlag Stuttgart.

Regioselective photochemical and microwave mediated monobromination of aromatic compounds using 2,4,4,6-tetrabromo-2,5-cyclohexadienone

Bromination of different aromatic substrates have been described using 2,4,4,6-tetrabromo-2,5-cyclohexadienone in conjunction with microwave and ultraviolet radiations. Important features of the work include high regioselectivity obtained in very short to moderate reaction time, atom economy, and recyclability of the reagent. Copyright Taylor & Francis Group, LLC.