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Relevant academic research and scientific papers

Nickel catalyzed deoxygenative cross-coupling of benzyl alcohols with aryl-bromides

A nickel-catalyzed cross-electrophile coupling of benzyl alcohols with aromatic bromides has been developed. This deoxygenative cross-coupling occurs under mild reaction conditions at ambient temperature affording diarylmethanes, or 1,3-diarylpropenes from benzyl allyl alcohols. The system demonstrated good chemoselectivity tolerating an assortment of reactive functional groups.

MoO3 supported on ordered mesoporous zirconium oxophosphate: An efficient and reusability solid acid catalyst for alkylation and esterification

A series of molybdenum oxide supported on ordered mesoporous zirconium oxophosphate (MoO3/M-ZrPO) materials with different MoO3 loadings (0–20 wt%) and calcination temperatures (500–900 °C) have been designed, synthesized and employed as solid acid catalysts in alkylation and esterification. The XRD, TG-DSC, H2-TPR, N2-physisorption and TEM characterizations were taken to investigate the structural properties and states of introduced MoO3 species. The influence of MoO3 loadings and calcination temperatures in catalytic performance was detailedly investigated and optimal catalytic activity was reached at 10 wt% MoO3 loadings and treated at 700 °C. Moreover, MoO3/M-ZrPO catalysts exhibited outstanding catalytic performance in Friedel-Crafts alkylation of different aromatic compounds and esterification of levulinic acid with 1-butanol. Furthermore, it was noteworthy that the catalyst had superior reusability and no noticeable declines were observed in catalytic performance even after seven runs.

Pd-catalyzed chemoselective threefold cross-coupling of triarylbismuths with benzylic bromides

An efficient palladium-catalyzed protocol was demonstrated for the chemoselective cross-coupling of functionalized benzylic bromides with triarylbismuth reagents. Under the established conditions, catalyzed by palladium in the presence of K3PO

Tin exchanged heteropoly tungstate: An efficient catalyst for benzylation of arenes with benzyl alcohol

The partial exchange of tin with the protons of 12-tungstophosphoric acid (TPA) results in a highly active heterogeneous catalyst for benzylation of arenes with benzyl alcohol as benzylating agent. The catalysts were characterized by X-ray diffraction, Laser-Raman and FT-IR of pyridine adsorption. The catalytic activity depends significantly on the extent of tin exchanged with the protons of heteropoly tungstate. The characterization results suggest the presence of Lewis acidic sites by the exchange of tin. The catalyst with partial exchange of Sn showed high benzylation activity, which in turn related to variation in acidity of the catalysts. The catalyst is highly active for benzylation reaction irrespective of the nature of substituted arenes and benzyl alcohols. These catalysts are highly active compared to other acid catalysts used for benzylation of different arenes. The catalyst is easy to separate from reaction mixture and exhibit consistent activity upon reuse. The plausible reaction mechanism based on the role of both Lewis and Bronsted acid sites of the catalyst was discussed.

Chlorine borrowing: An efficient method for an easier use of alcohols as alkylation agents

Chlorine functionalised tin dioxide nanoparticles proved able to partially convert alcohols into the corresponding chlorides, which act as alkylation agents with an increased electrophilicity, as evidenced on ether formation and Friedel-Crafts reactions.

Gallium Dichloride-Mediated Reductive Friedel-Crafts Reaction

In the presence of gallium dichloride, the reaction of carbonyl compounds or their dimethylacetals with aromatic compounds afforded Friedel-Crafts alkylated adducts in good yields.It was suggested that the adducts were obtained by way of a reduction of the carbonyl compounds or their dimethylacetals, followed by the Friedel-Crafts reaction in one-pot.This is the first organic synthetic method with gallium dichloride, low valent gallium.

Electrophilic aromatic substitution. 12. Kinectic studies of the TiCl4-catalyzed reactions of benzyl chloride, p-xylyl chloride, and p-nitrobenzyl chlordie with benzene and anisole in nitromehtane and dichloromethabe

Through the use of vacuum line techniques, noncompetitive and competitive kinetic data have been obtained for the TiCl4-catalyzed reactions of benzyl chloride and p-methyl- and p-nitrobenzyl chloride with anisole and with benzene in solvents ni

FRIEDEL-CRAFTS ALKYLATION OF ANISOLE AND ITS COMPARISON WITH TOLUENE. PREDOMINANT ORTHO-PARA SUBSTITUTION UNDER KINETIC CONDITIONS AND THE EFFECT OF THERMODYNAMIC ISOMERIZATIONS

The AlCl3 and BF3, as well as 65percent HPF6, catalyzed Friedel-Crafts alkylation of anisole with alkyl halides and alkohols was investigated.The alkylation of anisole with lower catalyst concentrations under mild conditions shows predominant ortho/para directing effect generally with a ratio of c.a. 2:1, with the amount of meta isomer uniformly less than 3percent.With "swamping" catalyst conditions the amount of meta substitution in methylation and ethylation can substantially increase.The isomer distribution in tert-butylation changes with time due to rapid ortho-para interconversion.Consequently, the AlCl3-catalyzed isomerization of isomeric alkylanisoles was also studied.In case of tert-butylanisoles, the ortho isomer shows relatively rapid conversion into para followed by much slower isomerization to meta.The para and meta isomers show isomerization to meta-para mixtures.Isomerization of ethyl-, isopropyl-, and benzylanisoles is generally slow whereas methylanisoles do not isomerize.Comparing results of the alkylation of anisole with toluene leads to the conclusion that the latter are readily affected by concurrent (and in some cases consecutive) isomerization.As the barrier for isomerization in the benzenium ion intermediates of the alkylations is higher in the case of CH3O- than CH3-substituted systems, anisole tends to give the kinetically controlled ortho-para alkylation products and the amount of meta isomer is low.Study of alkylation of 3,5-di- and 2,4,6-trideuterated toluene and anisole and comparing retained deuterium contents with isomer distributions shows that alkylated product formation in case of toluene, but not of anisole, is proceeded by intramolecular, 1,2-alkyl, and hydrogen-deuterium shifting resulting also in increased meta substitution.This effect is most predominant in methylation and ethylation where the alkyl shifts are intramolecular but not in tert-butylation and benzylation, where alkyl transfer is intermolecular.Isopropylation is intermediate in nature.No simple selectivity-reactivity relationship is indicated in the studied alkylation reactions.As shown in benzylations with increasingly electron-donating and -withdrawing substituted benzyl chlorides overall rate (i.e., substrate selectivity) and isomer distributions (i.e., regioselectivity) are not determined in the same step as significantly decreased substrate selectivity is not accompanied by loss of positional selectivity.Previously reported alkylations showing high degree of meta substitution therefore, must have been affected by thermodynamically controlled rearrangement processes, including intramolecular alkyl and hydrogen shifts in the arenium ion intermediates of the alkylation reactions.These are to be differentiated from possible subsequent product isomerizations.Under predominantly kinetic conditions anisole as well as toluene are substantially ortho-para directing in alkylations, as in other electrophilic aromatic substitutions.