The continued development of pharmaceuticals is related to the ability to form a wide range of chemical compounds. Diaryl ethers, characterized by the presence of an oxygen atom attached to two aryl groups, are a class of organic compounds with a wide range of applications, namely as a refrigerant and an antiseptic to prevent inflammation. diseases. In particular, diary ethers have become a topic of research interest because their organic synthesis is difficult. They can be made from aryl-alcohols, or phenols, when a second aryl group is converted to alcoholic hydrogen. But phenol O-arylation methods are not currently suitable and use transition metal catalysts (the more palladium catalyzed cross-coupling reaction won the prize for the 2010 Nobel in Chemistry). In addition, it is not selective, which means that many different side products are produced, reducing the effectiveness and end result of the desired organic compound.
Now, a research team from Ritsumeikan University, Japan, has suggested that metal catalysts be more sustainable. In this process, the conversion metal was replaced with a simple and easily synthesized precursor, trimethoxyphenyl (TMP) -iodonium (III) acetate. “This iodonium salt has two main functions, namely the TMP ligand and the acetate counterion, working together to increase the reactivity of the O-arylation reaction and, in turn, to improve the formation. the ether bond, which leads to higher yields of diaryl ethers.. than previously reported. It is a very good combination, “explained Assistant Professor Kotaro Kikushima, who author of the research. This paper was available online on March 7, 2022 and was published in Volume 24 Issue 10 of the journal. Organic Map and March 18, 2022.
Based on the properties of phenyl (TMP) iodonium acetate, the researchers predicted that diaryliodonium salt would have a higher reactivity. Therefore, the combination of the trimethoxyphenyl group and the anion acetate working together to increase the reactivity of the phenol oxygen atom was determined for the first time in their study.
The diversity and diversity of compounds is critical to the development of processes for future green, sustainable chemistry. To test the general nature of this method, the team tried and used different organic compounds for O-arylation. To their delight, they found that the texture and durability were very strong in a variety of processes, leading to a wide range of ethers blended with higher yields than the technologies described. a great consideration for professional applications. The possibility of increasing this process to business benefits has been shown by performing the response on a gram scale, maintaining a high efficiency. In addition to high -quality products and continuous starters the trend is also shown to have one good thing compared to current technologies: increased choice. The TMP group led to the selective arylation of the other working group, to allow more control, and no unwanted side effects.
“The current approach will provide a viable and secure market for a wide range of essential organic molecules under sustainable green conditions without the need for alternative metal catalysts. Our new goal is to innovate.” “Electrochemical and photochemical methods can be used to recover hypervalent iodine (III) and then can be used in another arylation,” said Professor Toshifumi Dohi, the lead author of the study.
The combination of these green innovations in the arylation solution has been shown to provide a sustainable synthetic method for the formation of stable bonds without the dangerous chemical degradation, a seismic change in continuity. of organic synthesis. With the interactions between the ligands and counterions shown, the green future of organic chemistry has not been considered.
Cross-linking effects: Semiheterogeneous PCN-Cu by metallaphotocatalysis
Kotaro Kikushima et al, Ligand- and Counterion-Assisted Phenol O-Arylation with TMP-Iodonium (III) Acetates, Organic Map (2022). DOI: 10.1021 / acs.orglett.2c00294
Presented by Ritsumeikan University
Directions: Scientists use a similar ligand-counterion system to create a continuous ether (2022, March 28) Retrieved 28 March 2022 from https://phys.org/news/2022- 03-scientists-cooperative-action-ligand-counterion- continuation.html
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