342794-86-9

Upstream product

• 207505-17-7 2-(trimethylsilyl)cyclohexen-1-yl triflate 
• 63617-45-8 2,5-diphenyl-6H-1,3,4-oxadiazin-6-one 
• 1499-10-1 9,10-diphenylanthracene 
• 523-27-3 9,10-Dibromoanthracene 
• 98-80-6 phenylboronic acid 

Relevant academic research and scientific papers

Cycloaddition Cascades of Strained Alkynes and Oxadiazinones

We report a computational and experimental study of the reaction of oxadiazinones and strained alkynes to give polycyclic aromatic hydrocarbons (PAHs). The reaction proceeds by way of a pericyclic reaction cascade and leads to the formation of four new carbon?carbon bonds. Using M06-2X DFT calculations, we interrogate several mechanistic aspects of the reaction, such as why the use of non-aromatic strained alkynes can be used to access unsymmetrical PAHs, whereas the use of arynes in the methodology leads to symmetrical PAHs. In addition, experimental studies enable the rapid synthesis of new PAHs, including tetracene and pentacene scaffolds. These studies not only provide fundamental insight regarding the aforementioned cycloaddition cascades and synthetic access to PAH scaffolds, but are also expected to enable the synthesis of new materials.

Ligand-enabled and magnesium-activated hydrogenation with earth-abundant cobalt catalysts

Replacing expensive noble metals like Pt, Pd, Ir, Ru, and Rh with inexpensive earth-abundant metals like cobalt (Co) is attracting wider research interest in catalysis. Cobalt catalysts are now undergoing a renaissance in hydrogenation reactions. Herein, we describe a hydrogenation method for polycyclic aromatic hydrocarbons (PAHs) and olefins with a magnesium-activated earth-abundant Co catalyst. When diketimine was used as a ligand, simple and inexpensive metal salts of CoBr2in combination with magnesium showed high catalytic activity in the site-selective hydrogenation of challenging PAHs under mild conditions. Co-catalyzed hydrogenation enabled the reduction of two side aromatics of PAHs. A wide range of PAHs can be hydrogenated in a site-selective manner, which provides a cost-effective, clean, and selective strategy to prepare partially reduced polycyclic hydrocarbon motifs that are otherwise difficult to prepare by common methods. The use of well-defined diketimine-ligated Co complexes as precatalysts for selective hydrogenation of PAHs and olefins is also demonstrated.

Chromium- and Cobalt-Catalyzed, Regiocontrolled Hydrogenation of Polycyclic Aromatic Hydrocarbons: A Combined Experimental and Theoretical Study

Polycyclic aromatic hydrocarbons are difficult substrates for hydrogenation because of the thermodynamic stability caused by aromaticity. We report here the first chromium- and cobalt-catalyzed, regiocontrolled hydrogenation of polycyclic aromatic hydrocarbons at ambient temperature. These reactions were promoted by low-cost chromium or cobalt salts combined with diimino/carbene ligand and methylmagnesium bromide and are characterized by high regioselectivity and expanded substrate scope that includes tetracene, tetraphene, pentacene, and perylene, which have rarely been reduced. The approach provides a cost-effective catalytic protocol for hydrogenation, is scalable, and can be utilized in the synthesis of tetrabromo- and carboxyl-substituted motifs through functionalization of the hydrogenation product. The systematic theoretical mechanistic modelings suggest that low-valent Cr and Co monohydride species, most likely from zerovalent transition metals, are capable of mediating these hydrogenations of fused PAHs.

Method for selectively catalyzing and hydrogenating polycyclic aromatic hydrocarbon based on cobalt salt

The invention discloses a method for selectively catalyzing and hydrogenating polycyclic aromatic hydrocarbon based on cobalt salt. According to the method, cobalt salt and methyl magnesium bromide are taken as catalysts, N-heterocyclic carbine or 2,2'-dipyridyl is taken as a ligand, tetrahydrofuran is taken as a solvent, polycyclic aromatic hydrocarbon is stirred to react under mild conditions in an H2 atmosphere, so as to obtain a hydrogenated product. Based on regulation and control of N-heterocyclic carbine or 2,2'-dipyridyl and synergistic catalysis of cobalt salt and methyl magnesium bromide, the high-selectivity hydrogenation of polycyclic aromatic hydrocarbon is realized under mild conditions. The method has the advantages of low cost, mild reaction conditions, high selectivity, wide substrate application range and the like and can be used for hydrogenating different substituted anthracene derivative and other polycyclic aromatic hydrocarbon substrates.

Deep hydrogenation of coal tar over a Ni/ZSM-5 catalyst

We have developed a Ni/ZSM-5 catalyst and utilised it to completely hydrogenate a series of condensed arenes, including naphthalene, anthracene and phenanthrene, under relatively mild conditions. The yields of decalin, perhydroanthracene and perhydrophenanthrene reached 100%, 98.8% and 25.8%, respectively. By analyzing the isomer distribution of the perhydroarenes, we proposed a mechanism of biatomic hydrogen transfer, which was further proven via the hydrogenation of 9,10-diphenylanthracene. Through hydrotreatment over the Ni/ZSM-5 catalyst, both high-temperature coal tar rich in condensed arenes and low-temperature coal tar mixing arenes with alkanes were greatly upgraded. The majority of arenes in the coal tars were deeply and even completely hydrogenated, which may open up a route for further processing and application of coal tar as clean fuels.