22926-97-2

Upstream product

• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 6921-34-2 benzylmagnesium chloride 
• 1712-69-2 1-isopropenyl-4-methoxybenzene 
• 100-63-0 phenylhydrazine 
• 100-44-7 benzyl chloride 
• 5281-18-5 benzaldehyde, hydrazone 
• 100-52-7 benzaldehyde 
• 100-39-0 benzyl bromide 

Downstream Products

• 5912-82-3 (E)-2-(4-methoxyphenyl)-1-phenylpropene 
• 1380439-41-7 (Z)-2-(4-methoxyphenyl)-1-phenylprop-1-ene 
• 22927-03-3 1-methoxy-4-(3-phenylprop-1-en-2-yl)benzene 
• 782-92-3 1-(4-benzylphenyl)ethanone 
• 17742-17-5 β-4-methoxyphenyl-β-methylstyrene 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Relevant academic research and scientific papers

Iron-Catalyzed Nucleophilic Addition Reaction of Organic Carbanion Equivalents via Hydrazones

Earth-abundant and well-defined iron complexes are found to be cheap and effective catalysts for a series of "umpolung" nucleophilic additions of hydrazones. The new catalytic system not only maintains the broad substrate scope of an earlier expensive ruthenium system but also attains chemoselectivity of different kinds of carbonyl groups. Furthermore, the iron catalyst enables this reaction at ambient temperature.

Influence of the methyl group at C=C bridging bond of stilbene on the longest wavelength maximum in ultraviolet absorption spectra

The compounds stilbenes XArCH=CHArY(XSBY) and 1,2-diphenylpropylenes XArC(Me)=CHArY(XSMBY) have bridging groups CH=CH and C(CH3)=CH, respectively, in which the C(CH3)=CH has a side-group CH3 at the carbon-carbon double bond. A series of XSMBY were synthesized, and their longest wavelength maximum λmax (nm) in ultraviolet absorption spectra were measured in this work. We investigated the change regularity of the νmax (cm-1, νmax?=?1/λmax) of XSMBY and compared it with that of XSBY. The results indicate that (1) there is no good linear relationship between the νmax of XSMBY and that of XSBY. (2) Because of the influence of the side-group CH3, in case of the same couple of groups X and Y, the λmax of XSMBY is shorter than that of XSBY, that is, it has a blue shift. (3) The cross-interaction between the side-group CH3 and Y has an important effect on the νmax of XSMBY, while the cross-interaction between the side-group CH3 and X has a little effect on the νmax and can be ignored. (4) The specific cross-interaction between X and Y has important effect on the νmax of XSMBY, whereas it has no important effect on the νmax of XSBY.

Iodine-catalyzed transformation of aryl-substituted alcohols under solvent-free and highly concentrated reaction conditions

Iodine-catalyzed transformations of alcohols under solvent-free reaction conditions (SFRC) and under highly concentrated reaction conditions (HCRC) in the presence of various solvents were studied in order to gain insight into the behavior of the reaction intermediates under these conditions. Dimerization, dehydration and substitution were the three types of transformations observed with benzylic alcohols. Dimerization and substitution reactions were predominant in the case of primary- and secondary alcohols, whereas dehydration prevailed in the case of tertiary alcohols. The relative reactivity of substituted 1-phenylethanols in I2-catalyzed dimerization under SFRC provided a good Hammett plot ρ+ = -2.8 (r2 = 0.98), suggesting the presence of electron-deficient intermediates with a certain degree of developed charge in the rate-determining step.

Aldehydes as alkyl carbanion equivalents for additions to carbonyl compounds

Nucleophilic addition reactions of organometallic reagents to carbonyl compounds for carbon-carbon bond construction have played a pivotal role in modern chemistry. However, this reaction's reliance on petroleum-derived chemical feedstocks and a stoichiometric quantity of metal have prompted the development of many carbanion equivalents and catalytic metal alternatives. Here, we show that naturally occurring carbonyls can be used as latent alkyl carbanion equivalents for additions to carbonyl compounds, via reductive polarity reversal. Such 'umpolung' reactivity is facilitated by a ruthenium catalyst and diphosphine ligand under mild conditions, delivering synthetically valuable secondary and tertiary alcohols in up to 98% yield. The unique chemoselectivity exhibited by carbonyl-derived carbanion equivalents is demonstrated by their tolerance to protic reaction media and good functional group compatibility. Enantioenriched tertiary alcohols can also be accessed with the aid of chiral ligands, albeit with moderate stereocontrol. Such carbonyl-derived carbanion equivalents are anticipated to find broad utility in chemical bond formation.

Intramolecular 10,10a-[2+2] photocycloaddition reactions of phenanthrenes with linked styrene

Intramolecular photocycloaddition reactions of styrene linked 9-cyanophenanthrenes led to formation of C-9 C-10 [2+2] cycloadducts which underwent cycloreversion under the prolonged irradiation conditions to regenerate the starting substrates. Unusual 8-membered ring products were irreversibly formed in these processes. Product distributions were governed by substituent controlled, donor-acceptor interactions that direct generation of two intramolecular singlet exciplexes, which serve as intermediates in the pathways to formation of 9,10- and 10,10a-[2+2] adducts.

Chloride-Bridged Dinuclear Rhodium(III) Complexes Bearing Chiral Diphosphine Ligands: Catalyst Precursors for Asymmetric Hydrogenation of Simple Olefins

Efficient rhodium(III) catalysts were developed for asymmetric hydrogenation of simple olefins. A new series of chloride-bridged dinuclear rhodium(III) complexes 1 were synthesized from the rhodium(I) precursor [RhCl(cod)]2, chiral diphosphine ligands, and hydrochloric acid. Complexes from the series acted as efficient catalysts for asymmetric hydrogenation of (E)-prop-1-ene-1,2-diyldibenzene and its derivatives without any directing groups, in sharp contrast to widely used rhodium(I) catalytic systems that require a directing group for high enantioselectivity. The catalytic system was applied to asymmetric hydrogenation of allylic alcohols, alkenylboranes, and unsaturated cyclic sulfones. Control experiments support the superiority of dinuclear rhodium(III) complexes 1 over typical rhodium(I) catalytic systems.

Iron-catalysed tandem cross-dehydrogenative coupling (CDC) of terminal allylic C(sp3) to C(sp2) of styrene and benzoannulation in the synthesis of polysubstituted naphthalenes

A novel iron-catalysed tandem cross-dehydrogenative coupling and benzoannulation process was developed for the synthesis of biologically and synthetically important polysubstituted naphthalene derivatives from simple 1,2-aryl-propenes and styrenes in moderate to good yields. The Royal Society of Chemistry 2012.

A mild oxidative aryl radical addition into alkenes by aerobic oxidation of arylhydrazines

A mild and practical oxyarylation of alkenes by oxidative radical addition has been developed by using aerobic oxidation of hydrazine compounds. The use of a catalytic amount of potassium ferrocyanide trihydrate (K4[Fe(CN) 6]·3 H2O) and water accelerated this radical reaction to give peroxides or alcohols from simple alkenes in good yields. The environmentally friendly and economical radical reactions were achieved at room temperature in the presence of iron catalyst, oxygen gas, and water. A method involving aniline as a radical precursor is also described. Copyright