What is it about?
Biaryls are molecules that have two carbon rings (known as “aromatic rings”) joined by a single bond. This type of structure is common in chemistry, and their production is therefore an important study area. One way to do it is through oxidative coupling reactions. In these reactions, the starting molecules lose electrons to an oxidant and then combine. However, strong oxidants and harsh conditions are usually needed. This makes the process more expensive and less practical. In this study, the authors found a new method to combine two aromatic rings called arenols into biaryls. The key to their approach is to use a catalyst containing iodine. The idea is that the catalyst splits and reacts differently with two independent arenol molecules. Then, these two intermediate molecules quickly combine with each other at the modified sites and form a biaryl compound. This happens thanks to the nature of the bonds they formed with the catalyst pieces. The authors also managed to use a similar method to join different types of aromatic molecules.
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Why is it important?
Biaryls are common in nature. They can be found in applications such as medicine and agriculture. Many of them are useful in industrial settings, including cleaning agents and for the creation of plastics. The proposed method is a simple way to synthesize biaryls and other aromatic compounds. A big advantage is that it does not require transition metals, which are costly. Another one is that the necessary reaction conditions are mild, and that the oxidant required is inexpensive and easy to obtain. KEY TAKEAWAY: Researchers found a more practical way to produce biaryls and combine aromatic molecules. Their results shed light on a new way to carry out oxidative coupling reactions in organic chemistry.
Read the Original
This page is a summary of: Hypoiodite-catalysed oxidative homocoupling of arenols and tandem oxidation/cross-coupling of hydroquinones with arenes, Chemical Communications, January 2021, Royal Society of Chemistry, DOI: 10.1039/d1cc05171g.
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