Chemists develop reaction cascade to produce fluorinated molecules

The step-wise construction of complex fluorinated molecules may require multiple purification steps. This has implications in terms of costs, time-management and the generation of waste. Dr Joel Häfliger and Dr Louise Ruyet from Ryan Gilmour's research group discovered that by fine-tuning the reaction conditions, multiple sequential reactions are possible in a one pot fashion. In this way, they generated three new classes of complex fluorinated products from simple cyclobutanol derivatives. "The strategy has parallels with the art of origami, where you fold complex figures from a simple piece of paper," Louise Ruyet illustrates. "This principle can be transferred to our chemical method.

The multiple folding steps represents successive reactions. "Starting with 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," says Joel Häfliger, the lead author of the paper. The key to the success of the approach was the use of an acidic medium to activate the substrate and produce an intermediate that can be intercepted by a catalytic cycle. The team synthesised a fluorinated analogue of the agent Nafenopin, which is used for hypolipidaemia -- a strikingly low lipid level in the blood -- as an application example.