101-53-1Relevant articles and documents
Alkylation on graphite in the absence of Lewis acids
Sereda, Grigoriy A.
, p. 7265 - 7267 (2004)
Graphite is introduced as a convenient catalyst for alkylation of aromatic compounds and alcohols by benzyl, tertiary alkyl, and secondary alkyl halides in the absence of strong Lewis acids. Primary alkyl halides are not active under the reaction conditions.
A New Ruthenium Catalysed Reaction. Benzylation of Functional Aromatic Compounds
Jaouhari, Rabih
, p. 1781 - 1784 (1994)
Ruthenium (II) and (III) complexes catalysed of the benzylation of functional aromatic compounds were described.Phenol, benzene and their derivatives were benzylated at 140-160 deg C, using a benzylhalide in non polar solvent or without it.
Extremely efficient cross-coupling of benzylic halides with aryltitanium tris(isopropoxide) catalyzed by low loadings of a simple palladium(II) acctate/Tris(p-tolyl)phosphine system
Chen, Chi-Ren,Zhou, Shuangliu,Biradar, Deepak Baburao,Gau, Han-Mou
, p. 1718 - 1727 (2010)
Highly efficient coupling reactions of benzylic bromides or chlorides with aryltitanium tris(isopropoxide) [ArTi(O-i-Pr)3] catalyzed by a simple palladium(II) Acctate/tris(p-tolyl)phosphine [Pd(OAc)2/ P(p-tolyl)3] system are reported. The coupling reactions proceed in general at room temperature employing low catalyst loadings of 0.02 to 0.2 mol%, affording coupling products in excellent yields of up to 99%. For benzylic bromides bearing strong electronwithdrawing cyano (CN) or trifluoromethyl (CF 3) substituents, the reactions require a higher catalyst loading of 1 mol%, or the reactions are carried out at 60°C. The catalytic system also tolerates (1-bromoethyl)benzene bearing β-hydrogen atoms while using a catalyst loading of 1 mol% to afford the coupling product in a 70% yield.
Mesoporous zirconium phosphate catalyzed reactions: Synthesis of industrially important chemicals in solvent-free conditions
Sinhamahapatra, Apurba,Sutradhar, Narottam,Roy, Biplab,Tarafdar, Abhijit,Bajaj, Hari C.,Panda, Asit Baran
, p. 22 - 30 (2010)
Mesoporous zirconium phosphate (m-ZrP) having high specific surface area and narrow pore size distributions is synthesized in basic medium using zirconium carbonate as source of zirconium. The concentration of phosphate in precursor solutions, as well as the calcination temperature, is found to influence the textural properties and acidity of synthesized m-ZrP significantly. Microscopic analysis indicates the presence of worm like pores with spherical morphology. The porous structure has remarkable thermal stability (up to 800 °C). DRIFT and NH3-TPD analysis suggest the presence of reasonable amount of Lewis and Bro?nsted acid sites. High catalytic activity of synthesized m-ZrP is observed towards Friedel-Craft (F.C.) benzylation reaction. The effect of acid strength of catalyst, reaction time, temperature and amount of catalyst towards Friedel-Craft benzylation reaction are also studied. The m-ZrP is highly active towards other acid catalyzed reactions in solvent-free conditions. The catalytic activity of m-ZrP is much higher than that of conventional layered ZrP. The catalysts were separated easily from reaction mixture, regenerated after a simple activation step and reused at least six times without significant loss in catalytic activity.
-
Monacelli,Hennion
, p. 1722 (1941)
-
Zirconia-modified superacid UDCaT-5: An efficient and versatile catalyst for alkylation reactions under solvent-free conditions
Yadav, Ganapati D.,Pathre, Ganesh S.
, p. 2684 - 2691 (2008)
UDCaT-5, a modified version of zirconia, efficiently catalyzes alkylation of phenols with alcohols under environmentally safe, heterogeneous reaction conditions with high selectivity and in excellent yields. The high content present in UDCaT-5 with preservation of tetragonal phase of zirconia was responsible for the superactivity. Several phenolic compounds carrying either electron-sulfer releasing or electron-withdrawing substituents in the ortho, meta, and para positions afforded high yields of the products. Copyright Taylor & Francis Group, LLC.
12-Tungstophosphoric acid/zirconia - A highly active stable solid acid - Comparison with a tungstated zirconia catalyst
Devassy, Biju M.,Halligudi,Hegde,Halgeri,Lefebvre
, p. 1074 - 1075 (2002)
A highly active and stable zirconia supported 12-tung-stophosphoric acid catalyst is found to be 2-3 times more active in benzylation and acylation reactions than a tungstated zirconia catalyst.
-
Kornblum,N. et al.
, p. 1141 - 1147 (1963)
-
Cytochrome P-450cam Monooxygenase can be Redesigned to Catalyse the Regioselective Aromatic Hydroxylation of Diphenylmethane
Fowler, Stephen M.,England, Paul A.,Westlake, Andrew C. G.,Rouch, Duncan R.,Nickerson, Darren P.,et al.
, p. 2761 - 2762 (1994)
A single-site mutant (Y96A) of the monooxygenase cytochrome P-450cam was found to bind diphenylmethane 5 and to catalyse its regioselective aromatic hydroxylation to p-hydroxydiphenylmethane 6.
Synthesis and catalytic activity of monobridged bis(cyclopentadienyl)rhenium carbonyl complexes
Li, Zhen,Ma, Zhi-Hong,Wang, Hong,Han, Zhan-Gang,Zheng, Xue-Zhong,Lin, Jin
, p. 647 - 653 (2016)
Thermal treatment of three monobridged biscyclopentadienes (C5H5)R(C5H5) [R?=?C(CH3)2 (1), C(CH2)5 (2), Si(CH3)2 (3)] with Re2(CO)10 in refluxing mesitylene gave the corresponding complexes [(η5-C5H4)2R][Re(CO)3]2 [R?=?C(CH3)2 (4), C(C5H10) (5), Si(CH3)2 (6)], which were separated by chromatography, and characterized by elemental analysis, IR, and 1H NMR spectroscopy. The molecular structures of complexes 5 and 6 were characterized by X-ray crystal diffraction analysis and show that both are monobridged bis(cyclopentadienyl)rhenium carbonyl complexes in which the molecule consists of two [(η5-C5H4)Re(CO)3] moieties linked by a single bridge, in which each of the two Re(CO)3 units is coordinated to the cyclopentadienyl ring in an η5 mode. All three of these monobridged bis(cyclopentadienyl)rhenium carbonyl complexes have good catalytic activities in Friedel–Crafts alkylation reactions.
Metal triflate formation of C12-C22phenolic compounds by the simultaneous C-O breaking and C-C coupling of benzyl phenyl ether
Hossain, Md. Anwar,Maihom, Thana,Mills, Kyle,Molley, Ashten,Rahaman, Mohammad Shahinur,Sathitsuksanoh, Noppadon,Tulaphol, Sarttrawut,Yelle, Daniel
supporting information, p. 17390 - 17396 (2021/12/10)
Catalytic pathways to produce high carbon number compounds from benzyl phenyl ether require multiple steps to break the aryl etheric carbon-oxygen bonds; these steps are followed by energy-intensive processes to remove oxygen atoms and/or carbon-carbon coupling. Here, we show an upgrading strategy to transform benzyl phenyl ether into large phenolic (C12-C22) compounds by a one-step C-O breaking and C-C coupling catalyzed by metal triflates under a mild condition (100 °C and 1 bar). Hafnium triflate was the most selective for the desired products. In addition, we measured the effect of solvent polarity on the catalytic performance. Solvents with a polarity index of less than 3.4 promoted the catalytic activity and selectivity to C12-C22 phenolic products. These C12-C22 phenolic compounds have potential applications for phenol-formaldehyde polymers, diesel/jet fuels, and liquid organic hydrogen carriers. This journal is
Insight into the chemoselective aromatic: Vs. side-chain hydroxylation of alkylaromatics with H2O2catalyzed by a non-heme imine-based iron complex
Ticconi, Barbara,Capocasa, Giorgio,Cerrato, Andrea,Di Stefano, Stefano,Lapi, Andrea,Marincioni, Beatrice,Olivo, Giorgio,Lanzalunga, Osvaldo
, p. 171 - 178 (2021/01/28)
The oxidation of a series of alkylaromatic compounds with H2O2 catalyzed by an imine-based non-heme iron complex prepared in situ by reaction of 2-picolylaldehyde, 2-picolylamine, and Fe(OTf)2 in a 2?:?2?:?1 ratio leads to a marked chemoselectivity for aromatic ring hydroxylation over side-chain oxidation. This selectivity is herein investigated in detail. Side-chain/ring oxygenated product ratio was found to increase upon decreasing the bond dissociation energy (BDE) of the benzylic C-H bond in line with expectation. Evidence for competitive reactions leading either to aromatic hydroxylation via electrophilic aromatic substitution or side-chain oxidation via benzylic hydrogen atom abstraction, promoted by a metal-based oxidant, has been provided by kinetic isotope effect analysis. This journal is
Phosphonic acid mediated practical dehalogenation and benzylation with benzyl halides
Gao, Jing,Han, Li-Biao,Ma, Yonghao,Tang, Zilong,Wu, Xiaofang,Xiao, Jing
, p. 22343 - 22347 (2019/07/31)
For the first time, by using H3PO3/I2 system, various benzyl chlorides, bromides and iodides were dehalogenated successfully. In the presence of H3PO3, benzyl halides underwent electrophilic substitution reactions with electron-rich arenes, leading to a broad range of diarylmethanes in good yields. These transformations feature green, cheap reducing reagents and metal-free conditions. A possible mechanism was proposed.
