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• 85-01-8 phenanthrene 
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• 53666-94-7 1,2-dimethyl-anthracene 
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• 858501-48-1 N-(3-benzyl-2,4,6-trimethyl-phenyl)-benzenesulfonamide 
• 954-16-5 2,4,6-Trimethylbenzophenon 

Relevant academic research and scientific papers

Deprotection of benzylic esters catalysed by anhydrous ferric chloride and rhenium carbonyl compounds

Anhydrous ferric chloride and [Re(CO)4Br]2 are shown to be useful reagents for the catalytic deprotection of benzylic esters. A suitable protecting group is p-MeC6H4CH2 with a working temperature of 5

Inversion in the Relative Reactivities of Mesitylene and Toluene in Clay-Catalyzed Friedel-Crafts Alkylation

Whereas toluene is more reactive than mesitylene when these substrates are benzylated separately by benzyl chloride, one-pot reactions in the presence of clayzic conversely favor mesitylene, with high intermolecular selectivity ( a factor 6-15).

A new layered MWW zeolite synthesized with the bifunctional surfactant template and the updated classification of layered zeolite forms obtained by direct synthesis

The medium pore-size zeolite MWW is very valuable as an industrial catalyst for aromatic alkylation and the first zeolite identified in the layered form. It shows extraordinary diversity by producing a great variety of different layered structures and forms: so far about 15 obtained by direct preparation and post-synthesis modifications, with 18 altogether recognised for all layered zeolites. We report a new layered MWW material, denoted UJM-1P (Uniwersytet Jagiellonski Material #1), which was obtained by prolonging synthesis of the mono-layered MWW material reported earlier, MIT-1. This transformation is new but not totally surprising. MIT-1 was obtained by using a special bifunctional structure directing agent (SDA) containing adamantyl head group and a long hydrocarbon chain. This strategy was applied first to produce by design layered forms of one of the most important zeolites-MFI. The MWW framework was previously obtained by direct synthesis in 5 different forms that could be rationalized by particular layer arrangements. MFI added 3 more types with two prepared, before MIT-1, with the aforementioned bifunctional SDA. MIT-1 and UJM-1P (as synthesized) and UJM-1 (calcined) are analogues of these layered MFI materials and are considered as the 6th and 7th MWW forms obtained by a direct one-pot preparation. UJM-1P has a multilayered slightly expanded structure similar to MCM-22P by with extensive layer disorder. It is easier to swell with surfactants than MCM-22P, which indicates weak interlayer connection that may be due to the special SDA molecules lining the surface of its layers. This is promising for delamination and formation of colloidal dispersions of MWW mono-layers. UJM-1 was confirmed to be a very active solid acid catalyst showing high concentration of Br?nsted acid sites of about 900 μmol g?1. It was tested in the mesitylene alkylation reaction showing high activity comparable to MCM-56, while MIT-1 was about 50% less active.

Cascade Reductive Friedel-Crafts Alkylation Catalyzed by Robust Iridium(III) Hydride Complexes Containing a Protic Triazolylidene Ligand

The synthesis of complex molecules like active pharmaceutical ingredients typically requires multiple single-step reactions, in series or in a modular fashion, with laborious purification and potentially unstable intermediates. Cascade processes offer attractive synthetic remediation as they reduce time, energy, and waste associated with multistep syntheses. For example, triarylmethanes are traditionally prepared via several synthetic steps, and only a handful of cascade routes are known with limitations due to high catalyst loadings. Here, we present an expedient catalytic cascade process to produce triarylmethanes. For this purpose, we have developed a bifunctional iridium system as the efficient catalyst to build heterotriaryl synthons via reductive Friedel-Crafts alkylation from ketones, arenes, and hydrogen. The catalytically active species were generated in situ from a robust triazolyl iridium(III) hydride complex and acid and is composed of a metal-bound hydride and a proximal ligand-bound proton for reversible dihydrogen release. These complexes catalyze the direct hydrogenation of ketones at slow rates followed by dehydration. Appropriate adjustment of the conditions successfully intercepts this dehydration and leads instead to efficient C-C coupling and Friedel-Crafts alkylation. The scope of this cascade process includes a variety of carbonyl substrates such as aldehydes, (alkyl)(aryl)ketones, and diaryl ketones as precursor electrophiles with arenes and heteroarenes for Friedel-Crafts coupling. The reported method has been validated in a swift one-step synthesis of the core structure of a potent antibacterial agent. Excellent yields and exquisite selectivities were achieved for this cascade process with unprecedentedly low iridium loadings (0.02 mol %). Moreover, the catalytic activity of the protic system is significantly higher than that of an N-methylated analogue, confirming the benefit of the Ir-H/N-H hydride-proton system for high catalytic performance.

Conversion of Aryl Aldehydes to Benzyl Iodides and Diarylmethanes by H3PO3/I2

For the first time, H3PO3 was used as both the reducing reagent and the promotor in the reductive benzylation reactions with aryl aldehydes. By using a H3PO3/I2 combination, various aromatic aldehydes underwent iodination reactions and Friedel-Crafts type reactions with arenes via benzyl iodide intermediates, readily producing benzyl iodides and diarylmethanes in good yields. Intramolecular cyclization reactions also took place, giving the corresponding cyclic compounds. This new strategy features easy-handling, low-cost, and metal-free conditions.

Preparation method of diarylmethane and derivatives thereof

The invention discloses a preparation method of a diarylmethane compound and a derivative thereof. In a protective atmosphere, heating reaction is carried out on aryl aldehyde and an aromatic hydrocarbon compound in the presence of phosphorous acid and elemental iodine to obtain diarylmethane and the derivative thereof. According to the method, cheap and green solid phosphorous acid is selected as a reducing reagent and an accelerant for reaction, the diarylmethane and the derivative thereof are efficiently prepared by a one-pot one-step method starting from a simple and easily available aryl aldehyde compound in the presence of elemental iodine, and the method has the advantages of simplicity in operation, cheap and easily available reagents, environmental friendliness and the like; use of expensive reducing reagents, metal reagents and transition metal catalysts is avoided, and industrial production is facilitated.

Cobalt-Catalyzed Kumada Coupling Forming Sterically Encumbered C-C Bonds

A Co(acac)3/PN precatalyst was developed and optimized for catalytic Kumada coupling of aryl Grignard reagents to sterically encumbered alkyl halides. The substrate scope demonstrates excellent yields for primary alkyl chlorides and bromides, including good performance using neopentyl chloride and neophyl chloride. Secondary alkyl halides were also successfully arylated in good yields, and the presence of β-hydrogen atoms in a substrate did not inhibit product formation. An intermolecular functional group tolerance screen was conducted which indicates that ester and amide functionality are well tolerated by the reaction conditions. Electrophiles containing ester, pyridine, and nitrile functionality were all coupled with 2-mesitylmagnesium bromide in good yields, supporting tolerance screen results. The intermolecular screen also showed that functional groups which are typically reactive with Grignard reagents such as alcohols and terminal alkynes were not well-tolerated by the reaction.

Mixed Alkyl/Aryl Diphos Ligands for Iron-Catalyzed Negishi and Kumada Cross Coupling Towards the Synthesis of Diarylmethane

Mixed alkyl/aryl diphos ligands have been prepared and their application in iron-catalyzed cross coupling of benzylic chlorides with diaryl zinc (Negishi) or aryl Grignard reagents (Kumada) towards the synthesis of diarylmethane has been evaluated. The iron?diphos catalytic system exhibited the enhanced activity and selectivity in the two coupling reactions. The electron-rich mixed PPh2/PCy2 ligands outperformed their symmetrical PPh2 congeners, and led to decreased homocoupling byproduct formation. It indicates that the electronic effect of the ligands plays an important role in the catalytic performance. The Fe catalyst supported by L8 bearing an electron-rich PCy2 substituent and a sterically demanding tert-butyl on ethene backbone exhibited the best catalytic performance and good functional group tolerance in the two cross coupling reactions.

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

Multifunctional oxygen vacancies in WO3–x for catalytic alkylation of C–H by alcohols under red-light

Surface reaction kinetics and light absorption properties of a photocatalyst are essential demands for efficiently solar to chemical energy converting. In this study, plasmonic WO3–x was firstly applied to photocatalytic alkylation of arenes under red light irradiation. The oxygen vacancies, both on the surface and in the bulk of WO3–x, allow abundant free electrons to increase carrier densities and support its LSPR using low energy photons. The surface oxygen vacancies have more functions: they not only release surface tungsten sites which ensure the chemisorption of alcohols due to the coordianation ability but also promote the activation of alcohols via an efficient transport of the holes on the neighbouring O sites to chemisorption alcohol species. In brief, the bulk oxygen vacancies provide abundant charges and the surface vacancies promote the bond adsorption and activation abilities, which ensure the high efficiency of photocatalytic alkylation of C–H.