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On July 19, Jiao Ning's research team at the State Key Laboratory of Natural Medicines and Biomimetic Medicines of Peking University published a new research paper entitled "Aromatic Ring Fragmentation to Alkenyl Nitriles" in Nature Online, reporting on aromatic ring selectivity Breakthrough research results in catalytic fracture transformation
.
Through the biomimetic design, the team proposed a cascade activation strategy, which solved the major scientific problem of the selective catalytic ring-opening conversion of inert aromatic compounds for the first time, and developed a new catalytic inert carbon-carbon bond activation mode, realizing a variety of anilines.
The conversion of easily available aromatic derivatives to alkenyl nitriles has achieved breakthrough progress in this field, or may provide new ideas for the promotion of coal liquefaction, biomass conversion, and petroleum cracking
.
Carbon-carbon bonds are the most basic structure that constructs most organic molecular skeletons.
The selective cleavage reaction can realize the direct modification and transformation of organic molecular skeletons.
It is also considered as a new generation of material transformation pathway
.
However, due to challenges such as high bond energy, low activity, and difficult control of selectivity, the cleavage and transformation of carbon-carbon bonds is one of the recognized problems in the chemical field
As one of the most basic structures of organic molecules, aromatic rings are widely present in drug molecules, functional materials and chemical raw materials
.
In the process of industrial production, the hydrocracking technology for petroleum aromatics cracking and coal-fired aromatics liquefaction usually relies on extremely high reaction temperatures, and the poor selectivity of aromatics' reduction and cleavage products limits the application of this reaction to a large extent
Jiao Ning’s research team designed a copper-catalyzed cascade activation strategy.
By producing highly active diazepene intermediates, it completed the highly selective ring-opening and cleavage conversion of a series of aromatic derivatives for the first time, and realized the conversion of high value-added olefins.
The high-efficiency synthesis of base nitrile compounds, and further reactions, can be used to prepare raw materials such as adiponitrile for nylon 66
.
This research not only realized the selective cleavage of aromatic rings under mild conditions, but also provided new ideas for the activation of inert carbon-carbon bonds
"To use a not very appropriate metaphor, our research results are like finding a way to cut jade
.
The aromatic ring is very stable due to its electronic conjugation properties, and it is difficult to open the ring and break and transform
It is understood that the efficient realization of this type of new reaction is expected to provide a new way for the high-value conversion of simple aromatic hydrocarbons from crude oil and coal, as well as for the degradation and utilization of biomass, and for the modification of functional material molecules and pharmaceutical active molecules.
