32250-86-5Relevant academic research and scientific papers
Intermolecular Friedel-Crafts reaction catalyzed by InCl3
Kaneko, Miho,Hayashi, Ryuji,Cook, Gregory R.
, p. 7085 - 7087 (2007)
Our recent discovery that In(III) salts were able to activate halides catalytically under mild conditions for the intermolecular Friedel-Crafts cyclization prompted us to explore this highly efficient activation in intermolecular Friedel-Crafts reactions. The alkylation of p-xylene with allylic and benzylic halides was demonstrated under catalytic and mild condition to afford in some cases quantitative yields of the monoalkylated products without the need to employ large excesses of reactants.
Friedel-crafts reaction of benzyl fluorides: Selective activation of C-f bonds as enabled by hydrogen bonding
Champagne, Pier Alexandre,Benhassine, Yasmine,Desroches, Justine,Paquin, Jean-Franois
supporting information, p. 13835 - 13839 (2015/02/05)
A Friedel-Crafts benzylation of arenes with benzyl fluorides has been developed. The reaction produces 1,1-diaryl alkanes in good yield under mild conditions without the need for a transition metal or a strong Lewis acid. A mechanism involving activation of the C-F bond through hydrogen bonding is proposed. This mode of activation enables the selective reaction of benzylic C-F bonds in the presence of other benzylic leaving groups.
InBr3-catalyzed deoxygenation of carboxylic acids with a hydrosilane: Reductive conversion of aliphatic or aromatic carboxylic acids to primary alcohols or diphenylmethanes
Sakai, Norio,Kawana, Keita,Ikeda, Reiko,Nakaike, Yumi,Konakahara, Takeo
experimental part, p. 3178 - 3183 (2011/06/28)
A simple and practical procedure for the direct reduction of aliphatic carboxylic acids with a variety of functional groups to a primary alcohol using the mild reducing reagent tetramethyldisiloxane (TMDS), in the presence of a catalytic amount of InBr3 has been developed. This simple reducing system, when used together with a hydrosilane, allows the preparation of the diphenylmethane derivative directly from an aromatic carboxylic acid and an aromatic compound. Copyright
High catalytic efficiency of nanostructured molybdenum trioxide in the benzylation of arenes and an investigation of the reaction mechanism
Wang, Feng,Ueda, Wataru
experimental part, p. 742 - 753 (2009/10/01)
The synthesis and characterization of nanostructured MoO3 with a thickness of about 30 nm and a width of about 450 nm are reported. The composition formula of the MP (precipitation method) precursor was estimated to be [(NH4)2O]0.169·MoO 3· (H2O)0.239. The calcination of the precursor in air afforded nanostructured pellets of the α-MoO3 phase. The nano-structured MoO3 catalyst exhibited high efficiency in catalyzing the benzylation of various arenes with substituted benzyl alcohols, which were strikingly different to common bulk MoO3. Most reactions offered >99% conversion and >99% selectivity to monoalkylated compounds. MoO3 is a typical acid catalyst. However, the benzylation reaction over nanostructured MoO3 does not belong to the acid-catalyzed type or defect site-catalyzed type, since the catalyst has no acidity and defect site on surface. Characterization with thermal, spectroscopic, and electronic techniques reveal that the catalyst contains fully oxygen-coordinated MoO 6 octahedrons on the surface but partially reduced species (Mo 5+) within the bulk phase. The terminal oxygen atoms of Mo=O bonds on the (010) basal plane resemble oxygen anion radicals and act as active sites for the adsorption and activation of benzyl alcohols by electrophilic attack. Such sites are indispensable for catalytic reactions since the blocking of these sites by electron acceptors, such as tetracyanoethylene (TCNE), can greatly decrease catalytic activity. This work represents a successful example of combining a heterogeneous catalysis study with nanomaterial synthesis.
Nanostructured molybdenum oxides and their catalytic performance in the alkylation of arenes
Wang, Feng,Ueda, Wataru
supporting information; scheme or table, p. 3196 - 3198 (2009/02/04)
We report for the first time that nanostructured MoO3 is an excellent catalyst for the alkylation of a wide range of arenes with substituted benzyl alcohols as alkylating agents. The Royal Society of Chemistry.
Synthesis of 1-aminoanthraquinone
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, (2008/06/13)
1-Aminoanthraquinone (1-AAQ) is synthesized by the reaction of 2-chlorobenzyl chloride and xylene in the presence of a solid acid catalyst to yield 2-chloro dimethyldiphenylmethane, subsequent oxidation of the methyl groups, ring closure to form a 1-chloroanthraquinone carboxylic acid, replacement of the 1-chloro group with ammonia, and decarboxylation.
SYNTHESIS OF SUBSTITUTED 2,4,5-TRIMETHYLDIPHENYLMETHANES
Pozdnyakovich, Yu. V.,Borodovitsyn, V. V.,Pozdnyakovich, S. A.,Shein, S. M.
, p. 353 - 359 (2007/10/02)
2,5-Dimethyldiphenylmethane and its 2'- and 4'-methyl, chloro, and nitro derivatives were obtained by the reaction of substituted benzyl chlorides with p-xylene in the presence of ferric chloride and zinc stearate.The yields of the 2,5-dimethyldiphenylmethanes depend on the nature of the substituent in the benzyl chloride and decrease with the substituents in the order NO2>Cl>H>CH3.The 2' and 4'-methyl, chloro, and aminoderivatives of 2,4,5-trimethyldiphenylmethane were synthesized by chloromethylation of the obtained diphenylmethanes with paraform in acetic acid in the presence of zinc chloride followed by reduction of the 2,5-dimethyl-4-chloromethyldiphenylmethanes with zinc in acetic acid.
