Fluorine is rarely found in natural organic molecules. However, this chemical element is essential for the production of pharmaceuticals or agrochemicals. Synthetic chemistry plays an important role in the creation of new molecular fragments containing fluorine. Simple, modular synthesis strategies are especially valuable.
A team led by Prof. Ryan Gilmour of the Organic Chemistry Institute at the University of Münster has now developed a cascade reaction that enables multiple fluorination reactions to occur through the sequential generation of reactive intermediates. Using inexpensive organic catalysts and simple starting materials, the group showed that the substrate can be manipulated through a type of “molecular origami” to create a new class of di- and trifluorinated molecules. in an operation. The study was published in the journal Communication in Nature.
The step-wise construction of complex fluorinated molecules may require multiple purification steps. This has implications in terms of cost, time management and waste generation. Dr. Joel Häfliger and Dr. Louise Ruyet from Ryan Gilmour’s research group discovered that by adjusting the reaction conditions, several sequential reactions are possible in a one-pot manner.
In this way, they created three new types of complex fluorinated products from simple cyclobutanol derivatives. “The strategy has similarities to the art of origami, where you fold complex figures from a simple piece of paper,” says Louise Ruyet. “This principle can be transferred to our chemical method.
Multiple folding steps represent sequential reactions. “Starting from our piece of paper—the cyclobutanol-derivative—an intermediate compound is produced. This compound can be processed into different products depending on the reaction conditions,” said Joel Häfliger, the lead author of paper.
The key to the success of the method is the use of an acidic medium to activate the substrate and create an intermediate that can be intercepted in a catalytic cycle. The team synthesized a fluorinated analogue of the agent Nafenopin, which is used for hypolipidemia-an unusually low blood lipid level-as an example of application.
Joel Häfliger et al, Integrating I(I)/I(III) catalysis in reaction cascade design enables the synthesis of gem-difluorinated tetralins from cyclobutanols, Communication in Nature (2023). DOI: 10.1038/s41467-023-38957-w
Provided by the University of Münster
Citation: Chemists create reaction cascade to produce fluorinated molecules (2023, July 13) retrieved 13 July 2023 from https://phys.org/news/2023-07-chemists-reaction-cascade-fluorinated-molecules. html
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